Ugly Duckling [F23] is paid to watch her boss jerk off. Fucks him for free. [FM]

Hi readers! For those of you that are reading all of my stories, this takes place post-bully during my sluttiest years when I tried to fill the…gaping…hole he left behind. During this time I met Tim, a dom I was with for about 8 months, mostly because he was my dealer and had a nice dick. He was possessive and not very fun so I didn’t see him much. He was also a creep. He offered to pay my rent if I just put a camera up in my living room so he could see what I was doing at all times. And since I was fucking random guys at least twice a month, I declined his horrific offer.

If you wish to skip to the sex, I’ll mark it XXXXXXXXXXXXXX.

TLDR: Sex.

In my last year of university, I took a job at this office where I could learn some valuable skills to help me get a job in my chosen field after I completed my post University college program. The company had two floors, one which was currently in use and another that was being renovated to be our new office. Once renovations were completed, there was a bit of an office shake-up in terms of where people were situated with the new layout. And I being the least useful to my direct superior was the furthest from them, but this put me closest to the Bosses office. So we began exchanging more pleasantries and talking about our lives more with each other.

Boss was probably 45 and owned the company, so he dressed however the hell he wanted. He had greying dirty blonde hair that he kept in a quaff-like mess, he wore glasses, and mostly kept up with fashion trends so he looked good and stylish but casual. He’s married to a beautiful Italian woman, very big personality and gorgeous dark hair and olive skin. Her makeup game was also flawless like I can’t get over how good she looked day to day and then could turn herself into a movie star when a big event happened. They have two kids together, both are close to the age of 10 and showed up to the office a lot. I bring this up, not for you to judge me for being a homewrecker (he made the first move, I don’t care) but because I’m genuinely unsure why he approached me in the first place.

My theory as to why this happened has to do with the summer BBQ we had about a week or two before these events, in which myself and several of the other younger staff members got really drunk. I remember being around my desk talking with a coworker (we had a patio for the BBQ) and we were talking about our relationships and she was talking about some rather kinky things without shame. Not to be outdone and no one else in earshot, I told her how I was fucking my dealer for pot (which wasn’t far from the truth). Eventually, I left and came back and noticed Boss leaving his office, I wasn’t sure if he was in there when I was talking, but I was embarrassed at the thought of it.

Maybe he turned on the charm after the BBQ, maybe it was always ramping up, but I know he put his hand on my shoulder more, and then the middle of my back. He also started to get more complimentary about my appearance, but NEVER around other people. Like if he caught me in the back hallway or downstairs checking the storeroom, he would tell me how great I looked and when he used the word “sexy” I knew he wanted me.

If you’d like insight into how my brain was wired in those days, as soon as I realized I could probably fuck my boss without affecting my future career, my brain started to fire off into a chorus of “FUCK YOUR BOSS! FUCK YOUR BOSS! FUCK YOUR BOSS!”

And once my slut-brain sets off on a task, I do it with gusto.

So I started being flirty back, touching his arm a lot, giggling more at his jokes, and even letting him ‘catch me’ looking at his crotch, only to look up and coyly shy (my signature move. 50% of the time, it works every time).

On a Thursday afternoon, I was tasked with helping to close down the old downstairs offices and arrange things for the sale of the old furniture. This was taking me longer than I expected and I was working late, probably around 6 when we usually had a hard 5PM exit at the office (pretty strict 9-5 place). The last to leave sets the alarm and that’s it. But I heard a call from upstairs “All Clear?” and it was too far to make out who it was so I replied back “No!” As loud as I could so they could hear me up the stairwell. Sure enough, I heard someone coming down the stairs and walking down the hall, and then my Boss was standing in the doorway.

“What are you doing here so late?” he said.

“Finishing the catalog for the sale. I’m almost done.” The room was mostly empty except for two desks and chairs and matching bookcases.

“I was wondering where you were all afternoon. We missed you upstairs.”

He started to ask me when I started college and how living with my roommates was going. And he even started to ask me if I was free from debt like it was some sage advice to not fall into debt. I actually wasn’t in debt, my father paid for my schooling and I just covered my living expenses. But I played it up to be a damsel in distress. (As I write this, I’m shocked how much I changed in a little over 4 years from losing my virginity. In this slutty phase of mine, I was a real man-eater, Woah oh here she cums)

To the best of my recollection, this is how he broached the subject:

“You know I caught you looking at my crotch the other day. What if I said you could make $500 just for getting a better look at it?”

I was shocked. I think my jaw was on the ground. He continued,

“All you would need to do is sit there and watch me jerk off and you walk out of here today, five-hundred dollars richer. If not, no big deal, either way, your job stays the same and nothing changes around the office. No harm no foul.”

I was already trying to seduce this guy for free but I’ve never received this kind of offer before. I sat back in my chair, a little proud of myself for some reason.

“Right now?” I asked.

“Right now.” He confirmed.

“Ok.”

XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

He set down his bag, went to the other desk, pulled out the chair so I could see it, and unbuckled his pants, sitting down. He folded up his button-up plaid shirt and tucked it up so it wouldn’t block the view of his dick. His stomach was quite hairy and there was a trail down that stopped at the waist, he had shaven recently. He pulled out his growing cock, cut, with an unusually small head, with a surprisingly bulbous shaft, that only got bigger as he grew harder. I sat watching intently as he played with himself.

As he grew, I rolled my chair out in the open so I could get a better look at him and he could see me better too. I was wearing a long black skirt that went past my knees, belt, plain black flats, and a pullover white blouse that tucked into my skirt. I leaned forward and put my hands under my chin and rested my elbows on my knees, this did two things: 1) It let me get slightly closer without moving my chair and 2) it let my loose blouse neckline fall open so he could see down my shirt, maybe see my bra. By the way, he groaned and jerked harder, I think it worked.

Fully hard he was about 7 inches and with the really bulbous thick part of his shaft beneath the undersized head. His dick also had a bit of a curve which I couldn’t tell from this angle, but it dipped down and angled back up so the head would rub against THE BEST PLACE if he fucks you in a certain way.

I picked up a few tricks watching my exhibitionist boss, if I made eye contact with him after looking at his cock, he’ll moan hard and if I lick my lips while looking at his cock, he’ll breathlessly say “fuck.” So I had a lot of fun watching, but it wasn’t enough.

I stood up at one point, he slowed down but he didn’t stop, keeping eye contact with me and then watching my hands intently as they both came up and undid my belt. His hand moved faster. I unzipped my skirt at the side of my waist and let the whole thing fall, leaving me in my red and white side-tie panties. He was stroking harder still, his eyes wide and burning a hole through the small slip of fabric preventing him from seeing my neatly trimmed pussy. I pulled my blouse over my head and tossed it aside, my white padded bra and little panties were all that remained after kicking off my flats.

I started to walk towards my Boss, he was only a few paces away but I took those steps slowly so my hands could untie my panties. When I was standing at his feet, I let my panties fall and he audibly gasped, reaching out, taking his hands off his cock, and putting them on my ass. He pulled me closer and I lifted my legs one at a time so I could straddle him on that shitty office chair. I carefully balanced on him and sank down onto his cock.

My breath was trembling as I tried to get the bulbous part of his cock entirely inside me, but it took a lot of effort, it was very thick. He was groaning and grabbing my ass hard, moving me just the way he wanted me to ride him. Slowly I got the entire cock inside me and I think I came a little when I could finally relax and just put my weight down onto him. I was hugging him tight at this point, his face in my chest (or lack thereof) and I could feel his hot breath spreading across my chest, warming me. I clung to him harder, wrapping my hands around his head and into his mess of hair, ruining it. I didn’t move much while riding him, mostly because he held me still, I think he was close to cumming and didn’t want it to stop.

After a while of this embrace, he stood up in a flash, taking me with him in a display of some rather impressive leg strength. He clearly took good care of himself but he was doing more than just staying in shape. He sat my ass down on one of the desks and started to fuck me hard. Looking right in my eyes, but I knew by now what he liked so I looked down and watched him fuck me, playing up my enjoyment of seeing his cock go in and out of me, “Oh fuck look at it…” I said in my best sex goddess voice.

I started off with the dirty talk because he wasn’t being terribly vocal and I like talking during sex.

“Am I a good employee for you, Boss?” (I actually called him boss, not his real name, giving him the power dynamic)

“Do you like fucking your slutty little intern?”

“I’ve wanted you for so long.”

And then he finally started talking. “You little whore, this is your new job, you are going to do this every week and weekend. I’m gonna work you overtime, slut.”

“Yes Boss, I’m so desperate for money, I’ll do anything you ask to keep this job.”

“I’m gonna cum inside you. Here it comes, slut.”

“Oh yesss Boss, give it to me. I want it all.”

After a few wild bucks of his hips, he started to cum hard inside me. His wife must have been blue balling him because there was SOOOOO much. Just gobs and gobs of it, possibly the most cum I’ve ever seen in my entire life.

We got dressed and he got out his wallet to pay me. He paid me $500, most of what he had in his wallet, and then tipped me another $20. The tip only made me feel cheap but I loved getting paid for what I just did. After we finished cleaning up and gathering my things, he walked me out and gave me a ride to a large transit hub that I needed to get to and was on his way home. He also told me to make a new email account, one the company didn’t have and any contact we had would be through that.

I fucked my Boss at that job for quite some time, he even sold my pussy to his friend who worked in the same building, just so they could trade parking spaces. My dealer dom never found out (hell I just ghosted him eventually, too psycho to deal with) and no one at work suspected I think. We had a great time so I may write more about him.

I hope you all enjoyed the story! As always, feel free to send any dick pics my way. They are always appreciated (and for goodness sake, that is my consent, so just send it, don’t ask permission).

Source: reddit.com/r/gonewildstories/comments/s3i19p/ugly_duckling_f23_is_paid_to_watch_her_boss_jerk