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Adult Confessions | If-the-boss-only-knew |
If The Boss Only Knew
You know how the saying goes "When the cat is away, the mice will play." Have you ever back stabbed a co-worker, peer, or EVEN your boss? Do you involve yourself in political game playing, office manuvering, or one-upsmanship games to advance your job position? Are you secretly gunning for the boss's job? Have you setup a fellow co-worker to take an embarrassing hit? Have you positioned yourself as an expert in subject matter you know absolutely nothing about? Have you thrown a fellow co-worker under the bus to secure a promotion? Have YOU been thrown under the bus?

Maybe your office place dealings are more sexual in nature.. Have you been involved in an office place fling with a co-worker behind your bosses back? Did your office place sexcapades lead you to a promotion, or ultimately get you canned? Adult Confessions is the place to share all the juicy details. Your boss will never be the wiser! ;-)
  • — If The Boss Only Knew —
    Straight Male / 26

    I had gone through a separation with plans for divorce while working as a police officer. My midnight dispatcher was a sixty five year old woman. She too was divorced twenty years back. I told her that I had not had sex with my wife for two months. She cried as if I were r****g her. When I stopped she said don't stop hurry and get it over.
    My dispatcher Anna said she had not have sex with a man since her youngest daughter was born. Her daughter was twenty two years old.

    Anna and I were walking out one morning when I stopped her, "If you want to have sex tonight, wear a skirt or a dress. if not wear pants.
    When I walked in the old shift was checking out, she looked at me and ask, How's my skirt look? I said great, then went on the road. I came in at 330am and brought Anna and I some food. Anna and I locked the building down from the inside. At the back kitchen and lounge area we sat at the table to eat. Anna took two bites of her food and sad this would wait till later. While I ate she got on the floor and opened my zipper.

    Let me see this dick that hurts so bad. She sucked and licked, I unhooked my sam brown belt and she tossed it in the chair. She opened my pants and pulled them off. She sucked my cock and licked my balls. She told me to cum now and she would get me hard again to fuck her. When my load released she choked a bit but eventually swallowed it all.

    She pulled off the skirt and opened her top. Unhooked the bra and her tits popped out. They laid flat against her. I am guessing at one time were massive, before they deflated. She laid back on the sofa and masturbated for me. watching this really old woman masturbate got me horny. My cock got hard with out her touching it. She ask me to come over, she was ready.

    I looked down as she spread the lips of her bald pussy and fed my dick in her. I could feel my cock hitting something up in her, but I had hit something in every woman I had been inside. Stroked her good and the same orgasm she had with her fingers came back. Then it got louder as she came. She said she was good if I wanted to cum in her thats ok. I grabbed her legs and put them on my shoulders, I started slamming cock in her hard. With each slam she moans out Oh and louder. Finally I was slamming her at a rapid pace and she was cumming loud and hard.

    She screams out Jesus Oh oh jesus and how good it feels. Finally she finished her second orgasm. I shot my nuts in her, for the 1st time in over two years I fucked without hearing my partner cry. I could actually fuck her without hearing stop it hurts or make it quick.

    I leaned to like working nights. Anna would leave work and stop by my apartment in the mornings, we would fuck for an hour or so and then she went home.

    That was over 25 years ago and I wonder if she ever thought about our times at work. The Chief ask me why I spent so much time in the office, I told him paper work and watching a TV show. He moved Anna to Day shift and moved Debbie a black girl to my shift dispatcher. By then I had a girl friend living at my apartment, I went home in the middle of the night for dinner and sex.

    #35286 — Comments (0) — May 14, 2017 at 8:58 PM — That's Juicy! (5) Remove This.
  • — If The Boss Only Knew —
    Straight Male / 20

    Haha, my boss is a complete tosser. He thinks by bullying me and messing my shifts about, he's in charge of my life. What the small dicked fat c**t doesn't know, is when he puts me on late shifts, knowing full well I've planned nights out with my friends and had to cancel, I call by his home and spend the morning fucking his beautiful younger wife. She loves hard horny dirty sex and says she can't get it from his tiny cock. So one afternoon at work with her picking him up, she flirted heavily with me. I tried my luck and asked her if she liked to fuck younger guys. The very next day I was balls deep up my bosses arsehole, as he was in meetings all morning.
    It's been eight months now since I first fucked his wife, and she's even now considering leaving the dickhead.
    I'm not the person she's leaving him for, she's leaving him for herself. But in the meantime I'm going to shag her as much as I can, because believe me, she's one hell of a dirty bitch.

    #35131 — Comments (3) — May 3, 2017 at 6:05 PM — That's Juicy! (10) Remove This.
  • — If The Boss Only Knew —
    Straight Male / 26

    He who laughs last, laughs longest. I believe that's the correct saying. Well I'm laughing longest now.
    My boss who's a tosser of the highest level of wankers, cancelled my leave so I had to work when I was supposed to be going on a weekend away with my mates. I later found out, he'd cancelled my leave so he could have the weekend off to take his wife out. Only on their weekend jaunt, they'd argued and she moved out of their home for a few days.
    Out with the same mates I was supposed to be away with, when they got back, I met a woman in her thirties who was obviously out for a good time. Walking up to us all, she asked everyone "Who's got the biggest cock". It was obvious she'd been drinking, but all the same I told her it was me (I'm not lying, I do have a large cock). Sitting next to me she put her right hand on my cock bulge and said "You'll do".
    One of my mates lives five minutes away from where we were drinking, so without asking him, he tossed me his keys and said "Have fun".
    He got back into his flat two hours later, as I was fucking the dirty bitch's arsehole one last time. We'd licked sucked and fucked and then fucked again and again. She was relentless and I was knackered by the time my friend got home. Dropping my second load of cum up her arsehole, having one already spurted down her throat earlier, she finally lay back once she'd frigged her clit making herself orgasm, as I slid out of her arse.
    Telling me I was good fuck, we swapped numbers and my friend got her cab. I got a text the next day and I met a sober, but very embarrassed woman in a cafe close to my home. She told me she'd fallen out with her husband, but didn't want anyone to know about our night together. All the same, she still came back with me to my place and had sex. It was more sensual, although she was still very much into having me fuck her arsehole. After showering with her and fucking her in the shower, I drove her over to her parents home.
    Now to the really good bit. In work two weeks ago I answered a call and told my boss, the wanker, his wife was calling in. Apparently they'd made up, but I already knew. Half an hour later I was stood face to face with the woman I'd already fucked twice and had arranged to have sex with that very night. Her husband my boss, tried to sound all authoritative with me stood there, but she told him to shut up. Like a told off puppy he slunk away as she winked at me. An hour later she text me to say her husband was going away, and that's why she'd called in to see him before he flew to London.
    Over the next two days with the leave I didn't get with him cancelling it, I stayed over at his house and fucked his wife over and over again. I even screwed her using his pillows to prop up her lower back, so I could enter her arsehole easier. And since he got back from his two day trip, we've fucked on five separate occasions, mostly at my place, but once in his car, fucking her on the back seat.
    He might have the power to cancel my leave or even to sack me. But it's me getting his wife in the sac, that's allowing me to laugh quietly at him each and every time I see him.

    #35071 — Comments (0) — Apr 28, 2017 at 1:48 PM — That's Juicy! (11) Remove This.
  • — If The Boss Only Knew —
    Straight Male / 24

    Just got back in from my bosses house. Only he wasn't there. He's down in London watching his team City playing in the FA cup semi final.
    As he was being driven down there, I was balls deep up his wife's pussy and arsehole. She's much younger than him and tells me he's shite in bed. So during a period when he was away on business a couple of months ago, she ran things. One of her first requests from me during that time, was to fuck her over his desk. I've been banging her ever since.
    She was such a slut today, she's always been a slut, I'm actually worn out from the amount of fucking we did. We ended up in their bed with my cock buried up my bosses wife arse. She got so into me fucking her shit hole, she began pissing all over the bed as she orgasmed.
    He he, good job she changed the sheets, otherwise he'd stink of piss tomorrow in work.

    #35004 — Comments (0) — Apr 23, 2017 at 10:33 AM — That's Juicy! (8) Remove This.
  • — If The Boss Only Knew —
    Straight Female / 44

    I started an affair with my boss recently, but of course he knows this.
    I have been with this company for about 7 years, but I will be quitting mid-June since a friend
    of mine offered me a job at her company then.
    My boss has always flirted with me, and my husband joked a few weeks ago that since I am leaving
    his company soon, I should flirt back.
    So, I did.

    What my boss does NOT know.....
    Is our affair is something my husband and I have talked about for a long time.
    My boss thinks I am secretly cheating on my spouse, but in reality its been my husband's plan
    all along. He has had a fantasy of me having sex with another guy since the day we got married
    it seems, but I have always rejected the idea.
    But I am in my 40s now and not getting any younger, so I decided to pursue things with
    Kenny, my boss since I had my husband

    Within 1 week of me flirting back to him, we were making out after hours. Which led to
    oral sex, and then the following week we started having intercourse.
    He has a wonderful cock, which I have described in detail to my husband.
    Its such crude, office sex though - either with me on the floor or bent over Kenny's desk.
    I hate to admit it, but its kind of exciting feeling like the "office slut" while my boss
    humps away inside me.

    We probably have sex 3 times a week, always after 530pm when most employees are gone.
    Kenny loves it when I call my husband while I am in his office, and say that I will be
    working late. He is usually undressing me or rubbing his cock in my face as I am
    But that is my husband's secret clue that I am about to have sex, and be ready for me
    when I get home.

    As soon as I get home, my husband is waiting for me in the bedroom.
    I undress and we get into a "69". My husband will literally spend about 15-20 minutes
    sucking all of my bosses' cum out of my pussy.
    If only Kenny knew that!! lol
    But it is pretty erotic to share something like that with my husband. As crazy as it
    sounds, we are closer as a couple because of the sex I am having at work.

    We are using my boss as a kink - but he does not have to ever know that.
    He is enjoying himself with me, I love how his cock makes me feel, and my husband gets
    his "sloppy second" fetish taken care of.

    Everyone is happy!

    #34989 — Comments (3) — Apr 21, 2017 at 2:35 PM — That's Juicy! (12) Remove This.
  • — If The Boss Only Knew —
    Straight Female / 20

    About 4 months ago, the office that I am an intern at hired a new staff member. He was SO cute, and I was SO into him. After a few months, I noticed him giving me a little extra attention. A little flirting here and there never hurt, right? Plus, he was so cute!

    I started to get the feeling that he was into me, until one day he was telling a story and casually mentioned his girlfriend. I was so confused! He had obviously been hitting on me, and it didn't exactly add up.

    Things started heating up a little bit more a few weeks ago; when at work, I spilt a bit of water on myself and said "Gosh, why do I only do stupid stuff when you're around?" When I asked this, he slowly took a step toward me and said "Because I make you nervous". I was SO flustered, but I was able to recover and ask him "And what makes you think that?" His response: "I don't know, you tell me." You could feel the sexual tension in the room. I left work that night thinking about how I'd like to have made a move at that moment.

    As time went on, he started hitting me up outside of work. Making plans and coming over to hang out, I figured we were just getting to know each other better! He is technically one of my bosses, even though the age difference is just a few years. I just thought we were focused on good friendship until one night he came over to watch movies.

    He sat on the couch next to me and as the movie went on, got closer and closer to me. First I noticed that our shoulders were touching. Then, our arms were intertwined. Then, he was holding my hand - rubbing my fingers with his thumb. I got up to go to the bathroom and when I was in there, I noticed that my vagina was dripping wet; just being close to him like this was turning me on.

    When I went back to the couch and sat down, he put his arm around me. I didn't know how to feel, so I attempted to break the tension with a joke. He teased me and when I accused him of being "Just like my 3rd grade bully" he said "Aw, I think you'll be okay" and then kissed my cheek. After that, he made eye contact with me, cupped my face, and kissed me on the mouth. The moment I had been waiting for for what seems like forever. I had prepared for this moment; I had told my best-friend/confident "If he ever were to make a move, I would pull back and remind him that he has a girlfriend, and if he ever wants to be with me, then he needs to break up with her first." I'd like to think that I have that much self-control. Yet in the moment; his lips on mine, his tongue gently pursing my lips open, and his hands still firmly cupping my face; any and all notions of morality and self-control slipped from my capabilities.

    He pulled me onto his lap; I was straddling him now. He kissed down my neck, his hands moving down my back and onto my hips. Breathing was getting heavier as we continued to let our kissing get carried away. He moved his hands from my hips to my breasts, enveloping them in both hands while still passionately kissing my neck.

    Again I had a flash of "I should stop this. This is dangerous. This is wrong." pop into my head. Yet as he moved one of his hands from my breast down to the seam of my pants and then inside to rub my clit, these reservations became my last priority.

    He rubbed me until I practically needed him to enter me. And then he did, just in time. His two fingers in me hitting just the right spot to make me yelp with pleasure. As he fingered me deep, I reached for his shirt and pulled it off of him. He removed his hand from my depths and did the same to me. Taking my now bare breasts into his mouth and moaning. As he did so, I reached for his waist.

    I slid down his length, leaving a trail of kisses down his chest until I reached the drawstring on his sweats. I let my mouth linger there for a few seconds, only to pull down his pants to reveal his penis. I kissed the tip gently, heard him sigh. Used the tip of my tongue to trace the head, and heard him lay his head back on the couch. Then when I took his whole penis in to my mouth, he exhaled deeply. I sucked and licked and kissed it now, with all traces of reservations completely gone. I knew what I wanted now, and it was too late to stop me.

    A few moments later, when I made eye contact with him to see if he was enjoying himself; he pulled my body up to him, kissed me hard on my lips and asked "Do you want to move to your bedroom?"

    He laid on my bed on his back, and when I climbed onto my bed to join him, I slid myself down onto his penis. At that moment, my whole body tingled. As I continued to ride him, moaning, I felt myself getting close to climax. My yelps got louder as he thrust in me over and over and over. I reached a point of no return, climaxing after only 2 minutes with his penis inside of me. At that moment, with one swoop of his arm he flipped me over and was penetrating me missionary style. My mix of yelps and moans now started to include whinny versions of his name; I was thoroughly enjoying myself.

    Next thing I knew, he had grabbed my legs from beneath him and pulled them up onto his chest. This allowed for the deepest penetration I have ever felt. My eyes widened; it almost hurt me. It was the good kind of hurt. The kind of hurt that I didn't want to stop. The thrust so hard into me and I felt him move in me. So so deep. So So good.

    Before I knew it, he had flipped me over again, laying behind me, both of us on our sides - and entered me from behind. One of his hands on my neck and the other gripping my breast. This was by far the best position he had put me in. He thrust and thrust in me until I orgasmed yet again, screeching with pleasure. As he kept going, I asked him in my out of breath, whiny, sex-voice "Are you gonna cum for me?". He grunted a determined "Yes" through his thrusts and then picked up the speed.

    My mind was in a place of disbelief, I had never ever had sex this good before. With a man who knew how to control the situation so effortlessly. I couldn't believe this was actually happening.

    As he kept going, faster now, he brought his other hand up to my throat - choking me. We stayed this way until he came in me, his thrusts slowing and eventually pulling out of me.

    We laid in bed catching our breath for a few minutes until I broke the silence and said "Well then". He turned his head to look at me, and sighed.

    Here we are, 2 days later and I can't walk without a limp. He left me so sore for the best reason. I can't wait to see what happens next; maybe sex on his desk at work.

    #34794 — Comments (0) — Apr 2, 2017 at 2:57 AM — That's Juicy! (25) Remove This.
  • — If The Boss Only Knew —
    Straight Male / 23

    My boss thinks everything is fine and dandy in his marriage. He's so fucking arrogant, he actually believes his twenty nine year old wife Jenny, enjoys having sex with his fifty five year old small cock. She tells me if he wasn't loaded, which he is, she wouldn't be within five miles of his cock. She's his second wife and he genuinely believes she's faithful to him. Jenny's a real fine looking woman, and is always at the gym. Which is where most of the men who've fucked her since they got married, have met her. That's because Jenny is a dirty cock loving slut. And this boy just so happens to have a really big cock. And when I say she's a dirty slut, I mean it. She loves nothing more than to be fucked in her mouth, pussy and up her arsehole. And she loves it rough too.
    We first fucked at the Christmas party last year. She cornered me in the function room at the golf club, where my boss is a senior life member, after donating a lot of money to improve the club. She asked me if the rumour was true about me. She'd spoken to a temp who'd let her know I'd fucked her on and off for a few months, telling Jenny I was well endowed. Pulling me outside in the cold night air, I was practically dragged over to the second green where she took out my cock and blew me, before she leaned against the flag pole and had me fuck her from behind. I swear I've never fucked a woman who wanted sex so badly. By the time I came inside her pussy, she'd climaxed twice, squirting both times all over my cock and balls and the green. Back inside, she was so calm telling her husband she'd shown me the facilities as I'd shown interest about becoming member. He smiled at his wife and looked at me like I was his new best friend. Little did he know later on when he asked me to give her lift, as he wanted to stay late taking a taxi home, that I'd be fucking his wife's arsehole in his very expensive car.
    Most weeks now when I'm not with my girlfriend, Jenny and I get together when and where we can to have sex. I know I'm just a young guy with a big cock to her. But then again, she's just my bosses wife who happens to be one hell of a dirty slut.

    #34743 — Comments (1) — Mar 28, 2017 at 1:31 PM — That's Juicy! (11) Remove This.
  • — If The Boss Only Knew —
    Bi-Sexual Male / 27

    I am a bisexual cross dressing sissy. Some call me a trap. But that is limited mostly to my social life. At work I dress in jeans, flannel plaid shirt and keep my long hair back in a pony tail. Some people shave Monday through Friday and let themselves go on the weekend. I do the opposite. I grow out my whiskers Monday through Friday and on weekends I shave close, put on make-up and can mostly just about pass as a girl though not quite as easily as I could when I was in school.

    So I work at a warehouse and my boss is O.K. I guess. I do data entry and do final checks on outgoing merchandise. So I work with carriers a lot and the pickers of course. My boss spends most of his time in the office but comes out to the floor from time to time.

    None of that really is worth talking about except for the fact that I bumped into my boss at a cross dressing party last week. Except he didn't know it. You see, when I go drag I don't look anything at all like myself when not dressed. But he didn't do a good job disguising himself. I recognized him immediately. At one point at the party he got on his knees in front of me and requested to choke on my cock. So I lifted up my skirt and pulled down my panties and stuck my 7 inch cock in his mouth. He sucked me until I came in his throat.

    He has on idea he gave a blow job to his shipping clerk.

    #34728 — Comments (1) — Mar 27, 2017 at 8:24 PM — That's Juicy! (1) Remove This.
  • — If The Boss Only Knew —
    Straight Female / 27

    My boss is a woman, and for a while I used that as an excuse to relax a bit in the office, not worry about my appearance as much. Which I couldn't do when I worked for a man. If I let my appearance slip he'd tell me I looked tired or start ignoring me altogether, and it's actually why he hired someone younger than me with half the qualifications but a shorter skirt and bigger tits before he even told me I was being let go for "poor productivity."

    An yway so working for her I felt much more secure, she wasn't about to fire me for skipping makeup one day, and that's still true.

    But one day I felt like dressing up for myself, wore higher heels, dug out a tight skirt, and left a few extra buttons undone on my blouse.

    I caught her sneaking looks all day. Mostly while I was facing away, but she nearly broke a pen when I brought in something that needed her signature and leaned down next to her to put it in front of her. After which, she "accidentally" dropped said pen which rolled away from the desk then asked me to pick it up for her. Then she told me to hold her calls for about an hour.

    So that's how I found out my boss was a lesbian.

    I decided to use this to my advantage. I started dressing like that every day, standing closer to her when I was at her desk or with her in the elevator, "accidentally" brushing up against her. One day I pretended to cry at my desk, then gave her a story about my boyfriend leaving me for someone prettier (I hadn't had a boyfriend in years) when she asked what was wrong. She reassured me that I was beautiful, he was a jerk, and gave me a hug, then we talked for a minute or two about men being awful.

    After that I started talking to her more when we weren't busy. At one point she asked me about my relationships. I think she was trying to be casual but it didn't really work, she asked me about my past boyfriends then kind of stuttered when she added "or girlfriends, whichever."

    I told her "well I've only ever been with men, but I mean every woman thinks about other women too, right?" She seemed to agree pretty eagerly.

    About a month later I was looking for an opportunity to ask for a raise. Our work was done for the day and we were talking and I brought it up. She said she wasn't sure. I went and sat on the edge of her desk, I told her I really needed the money to take care of my bills.

    She said she'd look into it.

    I rubbed her leg with mine and I asked if there was any way I could help her decide.

    She said she might be able to work something out, but she needed to evaluate my performance.

    I got down and sat in her lap sideways, I told her she seemed pretty satisfied with my performance so far. She didn't say anything, so I kissed her.

    She pulled me closer, ran her hand over my thigh, then broke the kiss and told me to go lock the door.

    Once I did, she asked me if I was just doing it for the raise. I told her no, which wasn't a total lie. I was mostly doing it for the raise, but honestly even though I'm not into women I had to admit the situation was turning me on anyway.

    She slipped out of her pants and had me eat her out first. I was kinda grossed out being face to lips with another woman's business, but once I dug in I got used to it. She said I wasn't that good, and if I expected a raise she expected me to get better at it.

    Then she laid me back on her desk and ate me out. It was honestly the best orgasm I'd had probably my whole life. But she wasn't done, she had me strip down to my stockings and lay on her desk while she played with me. Kissed me, fondled me, fingered me.

    I stayed naked in her office until the day was out, only a few people called for business over the phone.

    Since then I've gotten that raise. When we have free time we don't always fuck, but I've gotten better at eating out, she started keeping toys in her desk. Even when we're just talking we sit closer together, sometimes she has me put my feet in her lap and she massages them. Sometimes if she's busy but I'm not she likes me to be in the office with her. Today she was filling out paperwork, she gave me a vibrator and told me to use it until she needed me to do something.

    She wants me to consider moving in with her. She has a nice house and she lives alone, and it's not like I've really got anything going on outside of work, so I'm considering it. I consider myself straight, but I can make an exception. And besides, if I can do it, why not go from being just a secretary and living in a shoebox to also being a sugar baby and living in a nice house?

    #34707 — Comments (2) — Mar 26, 2017 at 8:22 PM — That's Juicy! (10) Remove This.
  • — If The Boss Only Knew —
    Bi-Sexual Male / 22

    When I was in college my dorm mate and I were friends well still are but I know a secret he don't know. Almost every weekend we would go to parties and somehow he would get his hands on some drugs and pass out or go loopy (depending on the type of drug he gets). I take us back to our room which is hard cause this guy is huge all muscle, over six feet tall sports guy. I throw him on his bed and I crash on mine. Sometimes on those nights he wakes me up thinking we're still att a party and somehow mistakes me as a girl, crawls into my bed and proceeds to push his luckily average dick into my ass without lube and fucks me. So here we are in our room me trapped in my bed under my hulk of a friend who is plowing my ass in his drugged up state thinking he's got himself a girl from one of our classes, always calls me different names when he fucks me.

    Sometimes its the nerd Suzan, or the cute lunch lady chelsie, or some girl from his hometown. But either way I'm enjoying his escapades not knowing he's fucking his friends ass and unloading his spunk into me or sometimes on me if he's just so eager, then he passes out on top of me. Then I gotta fight him limp body off mine and throw his ass into bed. Next day he starts bragging to me how he got some pussy last night at the party and keeps telling me I should loose my virginity soon or I will have a hard time getting any later in life. (Heh arogent prick)

    Well few years later and here we are we both got families of our own, we work at the same factory, I'm head of maintenance and he is the son of the CEO who writes my checks.... and I see how funny it is that he's all redneck hating on faggets, this and that, but only I know how much his dick really liked my ass when he is drugged out of his mind ;)

    #34699 — Comments (0) — Mar 26, 2017 at 5:32 AM — That's Juicy! (6) Remove This.
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