[MF] That time one of my bosses jacked me off at work

Howdy again! I usually take a longer break between posts here, but reading [this story](https://www.reddit.com/r/gonewildstories/comments/5bcs9e/how_i_found_out_that_showing_off_is_fun_fm/) got me in the mood to talk about a (very) brief early stint I had with semi-not-really-exhibitionism, and I said my next post would be a bit lighter, so here you go. This is probably the last crazy story I have (after this, the one about boinking a supposed lesbian, and acting out a rape fantasy, my sex life has been decidedly vanilla), so anything I post after this one will probably be a bit more run of the mill (like my second post). So enjoy!

I was 19, and I was living at home. Hadn’t yet picked a college, hadn’t yet really *thought* about college (much to my mom’s chagrin), so I was just playing a ton of videogames and making some money waiting tables. I’d worked at the same chain restaurant for three years (got my first job there at 16 as a greeter). It was okay because it was never terribly busy (except Sundays after church) and it was within walking distance from my house (didn’t have a car).

Basically, I was kind of coasting through life. At this point I’d never even had a real girlfriend – there were girls I “dated” for two or three weeks, but nothing really meaningful emotionally and nothing physically beyond some awkward below the belt hand stuff. Despite what you may think of me after reading my previous stories, I was not (and still am not, if you believe my wife) a cool guy.

I liked my coworkers though. The kind of awkward “admire you from afar” type of like that’s familiar to someone as socially stunted as I was back then. I mostly just hung around the periphery of the work social circle, observing everyone and laughing when appropriate. They were nice to me, but I wasn’t invited to many of the after-work parties.

For the next part to make sense, I need to explain a bit about the uniforms we wore (they were pretty standard chain restaurant fare, but just in case some of you need a refresher). The waiter uniform consisted of a short sleeve button-up shirt, jeans, and safety shoes. We wore a partial apron to carry our notepad and cash in; it was tied around the waist and the pockets were in the front (kind of like a fanny pack, but flat). The apron hung down in the front to just above the knees.

Anyway, this all started because one day I overheard one of the other waiters flirting with a hostess. She was responsive to it, and they began a bit of a back and forth. It started to get lewd, and at one point the waiter said something about how he’d had his dick out behind his apron all day and that she should take a peek. She didn’t (and he was most likely just bullshitting anyway), but that put a bug in my brain.

I will preface this next part by stating a few facts for you:

* I was kind of weird back then.
* I was really dumb back then.
* I lived and worked in kind of a podunk town.
* Our restaurant was the worst performing location in the worst performing district in the company. Even when it was busy, it was mostly dead.
* Our clientele was almost entirely senior citizens.
* I was dumb, but not stupid – I didn’t do this if there were kids in the restaurant.

That stated…

One day, I got it in my head to try the dick-behind-the-apron thing myself. I didn’t have a girlfriend, I was bored, I thought it might be a thrill, take your pick. I went into the one stall in the restroom, lifted up my apron, unzipped my jeans, pulled out my dick and balls (the whole shebang), and put the apron back down over them, triple knotting it to be safe. I checked and double checked in the mirror to make sure nothing was visible, then went out on the floor and worked my shift.

After washing my hands, of course. I’m not a monster!

I worked most of my shift like that. It was a weekday, so pretty slow, but I did get quite a kick out of it. Over the next month, I did it quite often – always during weekday shifts, when the crowd was minimal. There was something satisfying about kind of (but not really) having my dick out six inches away from someone’s grandma while she was telling me she didn’t want chives on her baked potato.

What can I say? The restaurant industry is a terrible place that turns people terrible.

Anyway, like I said, about a month goes by of me doing this. It becomes part of my routine; walk to work, scan the restaurant, go to the restroom, get my junk out behind my apron, start doing my job. I figured if I somehow got caught, I could just say that I must’ve rushed out of the bathroom and forgotten to zip up (dumb).

So one night, it’s just after closing and the place is empty. I’m there with one waitress, one hostess, one of the assistant managers (Debbie), the bartender, and one person on the food line (plus a couple kitchen dudes) – basic skeleton crew. The restaurant is mostly clean since it was slow, but there was one big top near the end of the night that we hadn’t cleaned up yet. I was out on the floor with the waitress getting it sorted, which involved adjusting the leaf and setting the table back to its original, smaller state. The tables there all had those self-storing leaves, where you just pulled the two halves of the table out, lifted the thing up, and pushed them back together to expand it, and reverse that to restore it.

So we get the table back in its smaller form, and me and this waitress are standing across from each other just chit chatting. I’m sort of leaning against the table, awkwardly trying to chat her up, when across the restaurant directly to my right I hear–

———————————————————————

“*GLIB!!!*”

I look over and see Debbie standing near the food line, looking at the table near my waist.

I suddenly become aware of a draft.

I look down and see that the front of my apron got caught in the table while we were adjusting the leaf, pulling it up quite a bit. The way I was standing, the waitress directly in front of me couldn’t see anything, but anyone looking at me from the side…

*Shit!*

I punched down on the apron, freeing it from the table. I shoved it back down over my exposed genitals, but it was too late.

“Back to the office. NOW.” Debbie was pissed.

I started my walk back to the manager’s office, the other employees not quite sure what had happened. I thought about trying to tuck everything back into my pants, but Debbie watched me the whole way back to the food line and then followed directly behind me the rest of the way. There was no chance.

*Shit. Shit. Shit. I’m going to get fired.*

I stood just inside the door of the cramped office. There was a small desk with an old computer, a safe underneath said desk, and a couple filing cabinets. There was one monitor showing the feed from the one camera we had – the one directly above the back door, just outside the office. It was close to the exit and not air conditioned, so it was always warm in there. There were no windows, save for a tiny, false-mirrored one on the door itself (people inside could look out, but nobody could look in).

Debbie walked in just behind me, closing the door. She sat at the computer desk. There was another chair next to the door, which I moved to sit down in, but Debbie stopped me.

“Nope. Stand up.”

Debbie was a bit older, in her late forties if I remember correctly. She had the accent, weathered skin, and kind brown eyes of a good ol’ country gal, her sandy blond hair always tied back in a ponytail while she was working. I’d never caught myself ogling her, but she had the exaggerated curves and ample bust of a woman her age – wasn’t terribly out of shape either. “Matronly,” I guess you could’ve described her as. She had a couple grown kids (three I think, just a bit older than me), and was divorced from their dad for many years. She was strict, but super nice. She actually sat in on my interview with the GM three years earlier when I got hired at 16. If I could’ve picked any one of the managers to *not* catch me, it would’ve been her.

I stood there by the door in that tiny, hot office, Debbie sitting maybe three feet away from me in that cheap chair. Her face had disappointment etched all over it. She stared me in the eye for what felt like forever.

Finally, she spoke. “Lift up your apron.”

I didn’t know what to do. I was worried about losing my job – for the first time in months, I actually *cared* about my job. So I did as I was told. I looked away from Debbie, reached down with both hands, grabbed the bottom of my apron, and lifted it up. My sweet kindly country gal manager was now getting an eyefull of my 19 year-old dick and balls.

My dick itself isn’t really anything to write home about, just about six inches give or take. My balls however, I’ve been told, are on the large side. I try not to talk too much about my dick in these posts, but I felt it might be necessary for the next part of the story.

Debbie shook her head. “Jesus Christ, Glib–” at this, I dropped the apron “–what the hell are you doing?”

I tried to stammer out the excuse I’d developed ahead of time. “I uh–I must’ve–I went to the bathroom and I think–maybe I was–I was in a hurry and I guess I forgot to zip up?”

She looked me in the eye again, her face incredulous.

“Bullshit, Glib. I saw those big balls, those don’t just fall out by accident.”

I was immediately taken aback by her directness and use of the word “balls,” but I stayed silent. At the same time, I felt some slight stirring behind my apron.

“You can’t do that shit, this is a family restaurant. What if a kid saw you? We’d get sued and you’d go to jail.”

I remained quiet, trying to meet her gaze. I wasn’t about to say *It’s cool, I scoped the place out whenever I wanted to do this, don’t worry about it*.

She continued.

“Do you *want* to be on a sex offender registry for the rest of your life?”

“No ma’am, I don’t.”

“Do you *want* to have to find a new job?”

“No ma’am.”

“Then cut that shit out right now.”

“Yes ma’am.”

I still wasn’t quite sure what was going to happen. I’d never been disciplined at work for anything before so my record was clean, but this seemed like a terminable offense if ever there was one.

“Okay,” she said.

There was a brief pause, a slight twitch, like she was going to turn her chair around and tell me to leave. Just a brief moment of hesitation, it seemed like, as she processed something in her mind.

“Now let’s put that thing away.”

She reached forward and lifted up my apron. The “stirring” I felt earlier had culminated in what we colloquially refer to as a “half chub,” and Debbie was now looking at my semi-erect pecker. With her other hand, she grabbed my balls and attempted to stuff them back through my zipper. She wasn’t looking me in the eye anymore, but her face was still stern.

I was stunned. My boss had her hand on my balls, and I knew at the time there was something vaguely *very bad* about it. Something about sexual harassment in the workplace, management coercion, etc. I was also a lonely nineteen year-old guy, and a woman had her hands on my balls. Common sense did not prevail here.

“Um–” I remember thinking her hands were softer than I expected. I was growing more erect by the second.

Debbie shook her head. “Well this ain’t gonna go back in there like this,” she said.

It probably could’ve, but I didn’t say so.

She sat there for a moment, sort of rolling and massaging my balls in her hand while she held my apron up with the other. She raised her gaze to look me in the eye again. Her face did not betray any sense of pleasure she may have been getting from the experience.

“Do you want me to take care of this for you so you aren’t knockin’ over salt shakers on your way out of here?” she asked.

My head was spinning. I had an idea of what she was asking me, but it didn’t make any sense. It was surreal.

“Ma’am?”

Her eyes did not waver and her expression did not change. “I ain’t gonna ask it again, Glib.”

Again, lonely awkward 19 year-old dude. It took me about half a second to decide. I adjusted my gaze above her head, to the wall behind her. “Y-yes please ma’am, uh…please.” I’m certain my voice cracked.

“Alright,” she said. She let go of my balls and grabbed my apron with both hands, rotating it around my waist until it was in a position where she wouldn’t have to hold it up anymore. She leaned over to her left and squeezed a generous dollop of Lubriderm or something similar out of a bottle on the desk (I assumed to keep hands moist while managers were flipping through papers).

She rubbed her hands together, distributing the lotion evenly, before returning her attention to my situation. She continued massaging my balls with her left hand (which felt even better now with the lotion), and with her right, she began stroking the length of my cock. Her eyes remained on what her hands were doing – no looking back up at my face.

I was speechless. For several reasons. For one, I’d just been caught with my dick out at work and instead of firing me, my sweet middle-aged manager was giving me a handjob in her office. For two, she was *really good at it*. As I said earlier, I’d had a couple handsy experiences with girls before, but nothing like this. Debbie was a professional. She had an even, full-length stroking motion with a twist in the middle, and she was rolling my balls in her hand like she was trying to center her chi. This was a woman who knew her way around a dick–very different from the girls I’d been fooling around with.

I got bold and reached down with my right hand, cupping her generous left breast.

She stopped stroking and slapped the back of my hand, looking me in the eyes again.”

“Nuh uh,” she said. “I’m the one doing the touching. Not you.”

“Okay…” I replied, sullen.

“Hands behind your back,” Debbie ordered, pointing a finger at my face.

I crossed my hands behind my back. “Yes, ma’am.”

She stayed frozen for a second, scowling and pointing, to drive the point home. Then she got back to her business. Her pace quickened and her grip on my balls tightened slightly. I had never had a handjob like this before.

Eventually, I felt that explosive sensation building up.

“Debbie, I-I’m going to cum,” I told her.

She cocked one eyebrow, but kept right on going. “Uhhh yeah, that’s the point,” she muttered. Her grip on my balls tightened even more, and she angled my cock slightly higher.

I stood stark still, holding my hands behind my back, as Debbie jerked me off faster and faster, my dick pointing straight at her face.

*No. Way.*

“Uuuhhhhnnnnngghhhhh!” I grunted as I began to shoot thick, ropy streams of semen onto my manager’s face. My hips rocked with each release, but Debbie managed to maintain control of the situation, catching the majority of my jizz around her nose and upper lip. She was only the second woman to let me do that in my life, but she took it like a champ.

Again, a real professional.

Her strokes slowed as she squeezed the last few drops out of my dick and let them fall to the tile floor. She reached over onto the desk and grabbed a handful of tissues, tenderly cleaning the lotion from my cock and balls. She threw the tissues away, then gently pushed my spent member back through the zipper into my pants and zipped me up.

Some of my semen dripped from her upper lip to her lower one. As she readjusted my apron, she casually licked it from her lip and swallowed.

My apron in place, Debbie clapped me on the waist with both hands and looked up at me.

“Okay, get out of here,” she said, my ejaculate still slowly dripping down her face. “Take the back door right there. Don’t worry about rolling your silverware. And don’t let me catch you with your pecker out again or you’re fired.”

“Yes ma’am. Uhh….thank you.”

Without waiting, I turned and walked out of the office, then out of the restaurant’s back door to the left.

Nothing like that ever happened between me and Debbie again – it was business as usual the very next day. She only worked at the restaurant for about another year after that and then she transferred to another store. I did hear rumors that she got fired from that location not long after for something to do with one of the waiters, but I never looked into it.

Source: reddit.com/r/gonewildstories/comments/5bfbej/mf_that_time_one_of_my_bosses_jacked_me_off_at