HER NEW BOSS

 

HER NEW BOSS

I had gotten in as a high level manager with a major company. We were multimedia, and raked 

in over a billion a year, so it was a pretty big deal. Now, we were also, primarily, a porn 

company… but that honestly didn’t bother me. 

My Mom had actually worked for the company most of my life, and she uh, wasn’t a manager, if 

you know what I mean. Which was why, when my new assistant told me that she’d been 

instructed to ask me who my favorite porn star at the company was, I thought it was a pretty 

good joke to give my Mom’s screen name. She had gone from the hot young thing, to their #1 

milf over the last 18 years, but she was still super famous and a face for many of the company’s 

current brands. 

So, I was pretty surprised when I got an email titled, “You arrogant bastard”. It wasn’t mean 

spirited or hostile. In fact, it was best summed up by the fact that the author, a peer, had 

included the phrase, “the stones on you…”. He went on to mention my favorite porn star, and 

told me that my request was probably going to be a dead end since she was one of the biggest 

names in the industry right now, but that my consolation prize was waiting for me in my office. 

Now, I was pretty fucking confused. What the hell was going on? But when I got into the office 

(pretty rare for me, I preferred to work from home. The office has a lot of, um, Charm? No… 

distractions.), there was going to be a surprise waiting. 

Nonetheless, I made the trip that Monday, and at first, I didn’t notice anything in my office. But, 

as I was sitting at my desk and working on some reports, I had a moment where I needed to 

grab some coffee and stretch my legs, so I spun in my chair, and… came face to face with my 

Mother’s picture. Autographed even.

Now, full disclosure, my Mom is hot as fuck. I mean, obviously, right? But growing up and 

accepting that sex work was just another kind of work, and that the porn industry had problems, 

but that was all industries; that was all just part of my Mom working in the industry. What I didn’t 

bargain for, was a big titted, flirty, fun, easy going Mom, who was utterly seductive in everything 

she did, without even trying. So, and this may strike you as weird, but I never actually saw any 

of my Mom’s porn.

My asshole buddies did, and they never hesitated to tell me how much they liked hanging out at 

my house and normalizing how cool and normal my Mom was... before going home to jerk off to 

one of her more explicit videos. Like, having a super hot Mom was hard enough, having a super 

hot Mom that my buddies could google sucking cock was a whole other thing. So, to keep 

myself from lusting after my own Mom even more than, I hate to admit, I already did; I avoided 

her work like the damn plague. 

So, when I say that I turned and saw my Mom’s picture, I don’t mean, I saw a tasteful head-shot 

that an actress might use to try to land a modeling part. I mean, I turned in my chair and was 

immediately confronted by a poster of my Mom, dressed like a lovely housewife. Except that, 

she was kneeling, had a cock between her tits, a face covered in cum, and she was winking at 

the camera. To make things even harder on me, the poster was for “Mom’s who fuck their 

Son’s”. Which, I was guessing, was a movie my Mom was in… yeah.

So, that answered an important question for me. Had my Mom’s rep gotten me in the front door 

here, when I hadn’t told anyone who I was. The answer, was apparently no. Because no one 

realized that the woman whose porn name I dropped, secretly had the same REAL last name as 

me, and it wasn’t a coincidence. So, I figured that, maybe her poster was hard to get, and I’d 

unknowingly asked for a copy of it? Or maybe it was taboo to ask for a poster of one of the top 

porn stars? Or maybe the guy in the email was just teasing me because the specific Milf I’d 

asked for was old enough to be my Mom, and, it turned out, did Mom Son porn? Or maybe it 

was the autograph, that made the most sense… 1st day on the job and I accidentally asked for 

the autograph of one of their biggest stars…

Whatever the reason, I did my best not to look at the poster as I worked in the office all day. I 

failed, but I did my best. In fact, I definitely fucking jerked off to it before I left. At Work! Yeah, not 

a great way to start my second week. Imagine getting caught? But fuck… I couldn’t help it. 

Despite my best efforts to never see or do anything sexual that she had done, Mom was still 

very much a fantasy of mine. So, suddenly being able to look over and see her smiling at me 

behind a face full of cum as she winked, nearly topless, would have been too much to resist 

even without the implied incestuous title. 

I’d love to say that I was strong, and that was the end of it, but the truth was I went from working 

from home everyday, to coming into the office at least 3 times a week. Could I have just 

searched for more, maybe even better porn of my Mother? Yeah… but I convinced myself that 

because I didn’t ask for this, I was still, somehow, innocent of that particular act. 

That said, despite fantasizing about my super hot Mom more often, the new job was actually 

going pretty great. Until, out of nowhere, I got an email, while in the office, from my Mom. She 

told me that she was in the building, and would be coming up to see me shortly. So, obviously, I 

fucking freaked. I panicked for a bit, but then I figured, in the central hub of a porn company, the 

truth might actually go over really well. So I asked her not to, because someone had put a 

picture of her up in my office, and I didn’t want it to be weird between us. But after a minute, 

Mom just texted me on my cell phone with, “LOL! It’s a signed copy sweetie! Who did you think 

autographed it for you? LOL!”.

That… was unexpected. But I guessed Mom had already seen the worst of it, and had just 

figured that it was pretty normal where she worked, and she wasn’t going to sweat it.  I had no 

idea how cool I was going to be with having her in the same room with that pic, but I couldn’t 

email or text back with, “Hey Mom, I actually jerk off to that signed photo of you an awful lot, and 

I think it might be weird if you were in the same room as it, since that would definitely make me 

hard for you.” Yeah. That might be tough to find the right words for. So, I made like the 

professional I was, and did my best to shrug it off. 

I like to think that I was doing fine too; at least, right up until Mom walked in. She knocked, I told 

her to come in, and she closed the door behind her. It was all perfectly polite and professional, 

except for the fact that she was wearing the same outfit/costume that she was wearing in the 

poster! She had red high heels, a tight skirt, and a black, button up blouse with entirely too 

many buttons undone. Even her damn hair was styled the same as it was in the poster. 

I was staring, I was red faced, and I could barely breathe. She was my Mom, and also the exact 

image that I’d been jerking off too at least 3 times a week, every week. She walked up to me 

with all the grace of a feline predator, and her laugh, though meant to be disarming, was SO 

sexual. 

She gave that laugh, and said, “Sweetie. Your face.” She was grinning widely as she bent over 

my desk, placed one palm on it, and with her other hand, reached over and, with one finger, 

lifted the jaw I’d left hanging open until it clacked back in place. 

I might, MIGHT, have recomposed myself in the face of her genuine mirth, but as she leaned in 

and lifted my jaw, I had a very clear view into her cleavage, and the sight of her nipples told me 

that she wasn’t wearing a bra. The knowledge left me squirming in place. Trying to adjust my 

cock without shoving a hand into my pants, and kind of failing. But, I was soon to learn that  I 

needn’t have worried. Mom laughed again at my reaction to her outfit, obviously loving every 

second of the attention, and then proceeded to explain to me the story behind the poster. 

It turned out that they had asked me who my favorite starlet was because it was tradition for 

people in my position, actress willing, to be “welcomed to the company” by their favorite 

pornstar doing their favorite pornstar things to them. But, because Mom was one of their best 

paid, most in demand actresses, my request had been like a Lt Governor saying they wanted to 

have lunch with the president. It was too much for my station. So, they’d gone to Mom, and 

asked if she would mind signing a poster for me instead. Then they told her my name… 

Immediately, Mom had known which poster in particular she wanted to sign for me. Then, after a 

few weeks, she’d reached out and told them that she had time after all, and was willing to see 

me, and give me a “proper welcome”. I got flustered all over again, but Mom calmly hushed me 

and with a hand-wave, she began to explain that it would be a really bad first impression to not 

only ask for too much on my first day, accident or not, but then also to be the only person at my 

level whose request has not been granted. On the other hand, she countered, if I shot for the 

moon, and got it, it would make a hell of a first impression. 

I couldn’t help it… I started to nod in agreement. After all, they were good points. She made a 

lot of sense, but I had questions. Like, how were we going to fake this, and what was expected 

of us. At that, Mom grinned at me again, and told me I was, “So cute”. Then she made her way 

around the desk, and hit her knees in front of me! 

I started to protest, but Mom literally told me to “Hush”, and, as she spun my chair towards her 

and began to work the opening in my pants, she told me what needed to happen. 

She explained that, when she left this office, she needed to be wearing my cum, for all the other 

managers to see. She would give them a flirty smile and a wink on her way out, and thus lay the 

foundation of my reputation as a man who gets what he wants. “Second”, she began to say. But 

no sooner had she started to speak then I moaned out, squirmed against my will, as she 

succeeded in fishing my cock out, and grasping it in her cool, delicate hand. She paused then, 

and gave me a smile to show me that she liked my reaction, then she continued. “Second,” she 

started again. “I do mostly Mom Son porn now, and let me tell you, it has made me more 

popular than I EVER was before. So, when your guy friends ask you if I ‘played Mommy’ for 

you, you are going to tell them yes. And,” she added, raising a finger to stop my protests. “... so I 

am I. So I hope you can understand how important it is that our stories match.” 

Then Mom was unbuttoning her blouse, and grabbing a bottle of baby oil, or some similar lube 

from her purse. She just started, oiling up her tits, casually, like it wasn’t the hottest, most insane 

thing in the world. As she did, she finished explaining her plan. “Those two things combined, will 

give you an in, but let me tell you, every man here thinks he is some kind of secret king in the 

bedroom, and they all have stories that only they tell (the implication being that the partners they 

claimed to have so deeply satisfied never seemed to mention it), yet you should totally believe 

them.” Mom was being super snarky with her tone, but it was hard to laugh at the joke when, 

within moments of telling it, she leaned forward, and slipped my hard cock into her oiled up 

cleavage. 

I moaned, loudly. I was closing my eyes, because I was afraid if I saw where that incredible 

feeling was coming from, that I would cum right away. But my chances of holding out dwindled 

real damn fast when Mom added, “and that’s why I’m going to come by again next week. So you 

can put me up against the wall, and give Mommy a good pounding that the whole office can 

hear. I’ll be super loud, and vocal, and refer to myself as your Mom, and every guy here will be 

both jealous and impressed.” She started to move her tits up and down then, stroking my cock 

as she gave me a slow, glorious titfuck. “And when they finally ask me why I came back, I’ll give 

them some line about how, I just couldn’t resist you, or how you were so commanding and 

handsome that when you told me to do something, I just couldn’t say no, or whatever. Trust me 

sweetie, they will eat that up, hook, line, and sinker; and you’ll be able to advance here with 

ease.”

I had my head thrown back, my eyes closed, and my tongue between my teeth as I struggled to 

make this heaven last as long as possible. Mom didn’t make it easy though. She was literally a 

professional at giving men pleasure, and the occasional flick of her tongue, or warm suck, or a 

lusty moan, only proved her incredible skill with each passing moment. Thankfully, she was 

going very slow. Easing me towards the edge of orgasm, but then stopping for a bit, and letting 

me cool off some before starting me up slowly again. 

She teased me to the edge and back a dozen times. But finally, I heard her say, “Sweetie… 

Look at me.”, and I knew that I had to listen, and also that, if I listened, I was going to lose it. 

But, I had no choice, so I opened my eyes, and gazed down at the hottest fucking thing I’d ever 

seen in my life. 

My Mom was looking up at me with lust filled, bedroom eyes. Her tits were oiled up, and, I 

hadn’t realized it, but I was “bucking” and my cock was sliding between them in part because I 

was actively fucking them. The front of her top completely open as she licked her lips and said, 

“There is no such thing as a subtle teenaged boy sweetie. I KNOW you’ve wanted this for 

years.” She looked every inch the porn star as she spoke. Beautiful, sexual, confident, and 

skilled. She held herself in a way so that I was looking my Mom in the eyes, but also having that 

image broken by the tip of my cock thrust up and out of her cleavage line over and over! Without 

meaning to, I started to buck faster, and Mom just smiled, gave an approving moan, and licked 

her full lips again, in a slow, calculated motion that made me thrust even harder. 

“That’s right baby”, she half moaned. “Look at me! Look at what you are doing to your Mother’s 

big tits! And that’s only the start. Your going to shoot your load all over my face, and I’m going to 

fucking love it! Then I’m going to walk out of here, and everyone is going to see your cum on 

me. And when I come back in a week, you are going to bend me over, and pound your Mother’s 

tight little cunt so hard that the whole office is going to hear me screaming about how big you 

are!” 

I couldn’t hold on one second longer, I started to warn my Mom that I was about to cum. But 

Mom didn’t hesitate. She shoved one of her oil covered hands up in between her tits to grasp 

my cock, and she began to jerk me off while her tits still touched me. She aimed the head of my 

cock at her face and told me to “Do it baby! Cum for me! Cum on Mommy’s face! Cum all over 

Mommy’s pretty face! Give all that hot young cum to Mommy sweetie!” 

And, I, Fucking, did! Whether or not they heard her, they definitely heard me. I came with a 

fucking roar! I screamed, and grunted, and growled, and bucked as my Mother hand jerked 

load, after load, after load out of me, and onto her! It took forever to finish, and when I was 

finally done, Mom looked like she’d been the center of a circle jerk! She had 10 times the cum 

on her that she’d been wearing in the poster. Then, as if reading my mind, she looked over at 

the poster, then back at me, and smiled. A second later, she dug out her phone, and snapped 

some selfies of her covered in my load. Then, standing, she buttoned a single button on her 

blouse, just enough to cover her nipples (mostly), and headed for the door. As she left, she 

promised to send me the pics; and then she shot me a wink, and walked out into the building. 

Looking ravaged, used, and cummed on. Which, of course, was her point. 

Sure enough, a week later, Mom shot me a text letting me know that she was in the building on 

a “surprise visit” again, and wanted to know if I was, in her words, “ready for her”. 

Fuck yes I was! 

 

Still though, even after all my fantasizing, and even after everything that had happened the 

week before; she was still, MOM!. With a capital “M”. So I hesitated. Like, how do you do… 

‘that’, with your own Mom. “Hey baby, come here often”, didn’t seem like it would do the trick. 

Thankfully for both of us, Mom had no such hang-ups. She closed the door, kissed me hello 

right on the mouth, and when her tongue slipped between my lips and she started to make my 

head spin with her kissing skills alone; she reached down and cupped me through my pants 

making me moan into her mouth. 

She she had me stranded between needing to sit down and wanting to take my cock out to 

relieve the pressure, she backed off from the kiss, gave me a seductive wink, and then in one 

deft motion she removed everything she was wearing from the waste up and dropped in all into 

a pile on my office floor. A second later she walked over to my desk, and with a flirty smile she 

beckoned me over to her with a curling finger on her left hand (the first time I noticed she was 

wearing her wedding ring and engagement rings). 

As I got close, she bent herself over my desk, mashing her own tits into it and forcing me back 

by pushing her ass into the front of me. Then she smiled at me, and gave her hips a few 

graceful rolls that had her stroking my cock in between the cheeks of her perfect ass, even 

though we were both clothed from the waste down. 

Then, as Mother’s do, she seemed to know exactly what was wrong, and exactly what to say in 

order to fix it. With a toss of her head, she flipped all her long beautiful hair to one side, then she 

glanced at me over the other shoulder and with a knowing smile she said, “Don’t think about it. 

Not yet. Just feel this,” she said, rubbing against me with her ass. “And then…” she continued, 

stepping back into me even more and spreading her legs nice and wide. “...Do something about 

it.” 

Every single instinct in me suddenly knew exactly what to do, and Mom or not, I had both of our 

clothes pulled down just enough to grant access a few seconds later. And a moment after that, I 

slid into the wettest, tightest, most incredible pussy I’d ever felt in my entire life. I didn’t know if it 

was just the taboo, or if she was legitimately the hottest body I’d ever felt by a long shot, but the 

reason didn’t seem to matter as much as the incredible waves of pleasure that were washing 

over my whole body as i worked my way deeper and deeper into her. When I was balls deep in, 

and experiencing the single greatest high of my entire life, I had an almost irresistible urge to 

just start pounding her as hard as I could. But… she was my Mom. So I tried to go easy at first, 

even though it was nearly fucking impossible. She felt so good, and I just wanted MORE. 

Deeper, harder, faster. I was literally inside of her and I still wanted her So Badly! 

I lost control for a second and I heard her nipple piercing actually clacking my desk as she tried 

to push herself up on her hands because her large breasts were pressing into the wood so hard. 

When I noticed, I tried to back off a bit, and Mom shot me a look like an angry predator that had 

just caught something stealing from it. 

“Don’t you DARE hold back!”, she scolded. “After a second, she took a breath, and composed 

herself. Then she flexed her muscles… inside, and I felt myself gripped by an already tight 

pussy. “Do you feel that?” She purred. I nodded in reply, unable to speak for a second. “That’s 

your Mother’s pussy, sweetie. Does it feel good?” I nodded, and managed a “Yes!” 

That made her smile. “Good,” she said soothingly. “Don’t you want to make me feel good too?” 

She said with a little bit of a whine in her voice, and I was nodding vigorously before she was 

even done. “Then I need you to think about where we are, what we are doing, and who I am 

baby. Because, I know, I do, I’m ‘Mommy’, and I put band-aids on skinned knees, and tucked you 

in at night. I get it baby, I really do. But… I’m also a dirty, sex-crazed, cock-loving porn star! I’m 

trying to get my Son to fuck me hard in the middle of his office, in the middle of the work day, 

because I want as many strangers as possible to hear me screaming about how good a 

pounding my tight little cunt is taking. So, sweetie, baby, honey… I ADORE you. And you will 

always be my Baby boy. But right now, I need you to treat me like the whore I am. Do you think 

you can do that baby?” 

At that, I took in a deep, steadying breath; drew back till I was almost out of her, and then 

slammed back in!

Mom grunted, and moaned loudly. Then she smiled back at me, wickedly, and with an 

absolutely intoxicating look in her eyes, she said, “harder”. So I did it again, but even harder, 

and this time I actually knocked her off her hands for a second, and she was back to having her 

tits mashed against the top of my desk. But she just gripped the sides, and with a whimpering 

tone, she begged, “More”. 

So I gave her more. I started a slow, steady build of fucking her pussy just about as hard as I 

fucking could. A slow pace, but brutally powerful thrusts then knocked her whole body up and 

forward with each, slamming thrust. The next time she spoke it was all whimpers and moans as 

she asked weakly, “Am I acting like a dirty slut?” So I told her she was, and slammed into her 

again, making her moan and cry out. “Do you think your Mommy is a whore now?”, she asked, 

practically breathless. There was a begging to her questions. She was desperate to hear me 

say it. To tell her what a dirty whore she was. To remind her that people could hear her getting 

fucked by her Son. To promise her that she was going to cum on her Son’s cock, and then he 

was going to make her suck it clean. And with every filthy phrase, she moaned louder, and 

came harder.   

We started with her bent her over my desk, and didn’t stop until the top of it was badly scratched 

up by the piercing on her nipples (markings that I would later treasure). But we didn’t stop there. 

Later I put her up against the wall, then against the street facing window, and even against the 

door leading back out into the office. I pounded my own Mother’s tight little pussy until neither 

one of us could stand or walk without serious effort; and we finished with her telling me to “cum 

inside”. 

Later on, to my delight, she texted me a week after that and said that, even though she was out 

of town on a shoot, she was hoping to “visit me in the office” again soon. 

Honestly, my life just got better and better from there. I thought, honestly, as I got promoted, 

climbed the ranks, and got closer than I’d ever been with my Mother, that I had reached a point 

where I could not be surprised anymore. 

But the truth was, though I’d been promoted twice in the same year, I was still the new guy, and 

had yet to see how things at my new company worked. Thankfully, I had Mom to advise me. 

Which was why when December’s cool weather rolled around, she sent me a warning email. 

She told me that, part of the whole initiation thing had yet to play out. 

She then informed me that, actress willing, part of the way the upper managers reminded new 

hires that they were special, but not irreplaceable, was a callback to that first offer. She 

explained that, the guys always felt like they were king of the world after they’d had their favorite 

porn star as their personal porn star (and I couldn’t possibly disagree). But then, whoever they 

requested, always got invited back for their first company Christmas party, this time as a party 

favor. That way, they could see that she wasn’t theirs, and also be reminded that it wasn’t their 

own power that had called her to them the first time either. 

That… left me reeling. But if I thought that was a lot, then I hadn’t properly braced for the real 

shocker. Because, as my Mom explained, though she had only been “That girl” one other time, 

because of the unique nature of her role in the company… well, they’d all pretended that she 

was the guy's Mom.

So yeah… At the office Christmas party, there was going to be dancing, and music, and eggnog 

and mistletoe. Then, as part of some good-natured office antics, my bosses, fellow managers, 

and some of my underlings were going to invite my Mother in to surprise me. Then they would 

dance with her, and play it off as normal at first. Then they were going to play with her tits, then 

finger her. It would also seem natural, but it would be planned. Things would devolve, and she’d 

end up giving someone a blowjob. Then two someones. And then, then they were going to fuck 

her. They were planning on gangbanging my Mother right in front of me, and they were going to 

laugh about it, and “pretend she was my real mom”. They were planning talk to me about how 

they were gangbanging my pornstar Mother, while that was exactly what they were doing! And 

my Mom? Well, she was a porn star who LOVED her work. So naturally, she was going to love 

every second of it, and it was going to show.

 

Ever seen your Mom put on a sexy little Christmas outfit and be flirty at a work party? Ever seen 

her still wearing what was left of that outfit, while your boss, and a few of your new friends made 

her airtight on a meeting table to the cheers of a horny crowd; while she moaned like a whore 

for more? Because I have.

And to be honest… it gave me ideas.

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(Bonus Pic. This one helped to inspire this story.)