Throwaway because not my proudest moment, but I thought you guys might get a kick out of it anyway. So this all happened a number of years ago, I had just started my first real job out of college and was engaged to my high school sweetheart. Life was good, money was good, the sex was great. Alas it was all too good to be true, I caught my wife to be with her mouth full in a club restroom. Looking back now I’m glad I dodged that bullet but at the time it broke me, my whole life spiralled from there on. Deep depression set in, my work suffered and they fired me, I stopped going to the gym and started eating and drinking more. It was a dark time but after some professional help I started to improve and get my life back on track.
Eventually I landed another decent job in the big city, moved and tried to start fresh and put all my woes behind me. I was on the up again, back at the gym, making good money and new friends. I wasn’t ready to start dating or open myself up again, my fiancé was the only woman I’d ever been with. Bar the odd teenage hookup with a finger and handjob, she was the my first and only. Sure I tried some tinder dates but I was always to nervous to seal the deal, even when the opportunity was there a couple times.
A few months go by and I get a promotion at work, moved to a new department and get a new boss, let’s call her Karen. She was no nonsense, tough, mean and god help you if you got on the wrong side of her. Half the office was terrified of her and she alway got her way, I was well aware of her even before I moved departments. She was much older than me, early 50s, divorcee, always well dressed, attractive but her years had begun to catch up with her. Luckily for me she was in a good mood my first day under her and she seemed to take a shine to me, eventually moving me further up the ladder and working more closely with her.
We became closer and her mean hard shell would soften and weaken when she got to know me more, it started innocently a hand on my shoulder as she walked past my desk, light arm massages as she peered over looking at my screen. At the time it felt safe and warming, not having any real physical touch for so long I welcomed her advances. More time passed and she got more brazen, touching got more frequent and the odd complement here and there. Commenting on how my body felt, gym was doing wonders, how I must be fighting the girls off every night. It was a great confidence boost at the time, but the more I read into it the more it made me slightly uncomfortable.
Her touching had become a daily routine, so much so that coworkers were joking about me getting my daily neck massage. Another promotion and I was moved to the office next to hers, that’s when the rumours started. I heard whispers of me sleeping my way to the top, she heard them too and seemed to actively encourage the rumours. From then on she was very flirty, looking back she was flirty from the beginning but me being the typical 23 year old male I was oblivious to it. It was fine and fun for the first few weeks but the more time that passed the more uncomfortable I got, she was openly calling me her “toyboy” to the office. Grabbing my ass and rubbing my upper thigh as she lent over to double check something on my computer, I’ll admit I got a semi on a couple of these occasions and I could tell she knew.
It all built up until one evening I was working late, she called me into her office and told me to have a seat. Closing the door and blinds behind me, she walked up behind me and started to massage my neck and shoulders like so many times before. Only this time she was firmer and more forceful, her thumbs working deep into my muscles. It felt amazing after a long day sitting hunched over at my desk, even let out a few slight moans as she pushed into tight knots. She lent over and started whispering in my ear, nice soothing tones telling me to breath and relax. Her hands began to move further down my body onto my chest and abs, unbuttoning my shirt as she went. He whispers then got more flirty, complimenting my body and getting more and more seductive. Even going so far to bite my ear ever so slightly, in all this intimacy my cock had decided to pitch a tent in my pants.
Of course she commented on that too, telling me to take my cock out for her. I was hesitant at first but she had a way about her that you knew not to make her ask twice, her whole mannerisms changed and she became more forward and dominating. I did what I was told and took my cock out, she continued to massage me as she stood behind me. She instructed me to slowly jerk it for her, as she watched over my shoulder and continued to rub her hands all over my exposed torso. I was working towards orgasm when she told me to stop, grabbing my hand and pulling it way from my cock.
She walked towards the sofa in the corner of her room, hiking her skirt and slipping of her panties as she told me to come to her. I got up and started walking towards her, her legs spread wide inviting me in. She again told me to stop, “crawl” she ordered. I got on my knees and slowly crawled towards her, her hands meeting my head as she guided me towards her neatly trimmed bush. Now I was no expert in giving head as my ex wasn’t a fan, but I gave it my best. She continued to instruct me and control my head, I worked my tongue in and around her as she demanded. Following her instructions until she had her tights wrapped around my head and orgasming loudly. My jaw hurt, my lungs hurt, my head hurt but most of all my cock hurt, begging for release.
She had other ideas, she fixed herself up and got behind her desk again and dismissed me as if nothing had happened. I was in shock to say the least, stuffing my fully erect cock back into my pants and shuffling out the door. Back at my desk I tried to comprehend what had just happened, but the lack of blood in my brain only had me thinking of how I needed to cum. Rushing home I jerked off multiple times that night, before going to bed.
The next week she acted like nothing happened, no friendly massages, no compliments, she was cold and distant. I was confused and still questioning to myself how it even happened, getting shoot down anytime I tried to bring it up with her. A couple weeks later I get an email from her, meeting in her office at lunch time. When I arrived it was only the two of us, she again closed the door and blinds. Told me to get on my knees and crawl towards her again as she pulled her panties to the side and revealed herself to me. This time she was fully dominant, no pleasantries, no nice warm up, only orders. I was hesitant again, this wasn’t like last time when it was late and the office was practically empty. This was different, she was different. But I gave in to her demands and again she was orgasming as my tongue explored her neither regions.
This became a regular thing, she would snap her fingers and I would be on my knees pleasuring her. It started off once a month, but over time became a weekly thing. She either ordered me to jerk or give her head, she never touched my cock or let me cum. Even though the promise of more was alway there she never for filled those promises, naive me always thinking this time she will let me cum, this time she will jerk me, this time she will blow me, but never coming to fruition.
At the time I was naive and perhaps a little immature to see the bigger picture, but eventually after much to long I realised I was being used. I was simply a play thing for her, she had no intentions to reciprocate or care about me. I decided to call her out on it, but her dominating manner left me feeling so small and helpless. Humiliating me for even considering that she would reciprocate, things stopped for a time after that. She became a tyrant, making my work life hell. But slowly but surely she weaselled her way back in, me being a weak hopeless male in not a great mental state letting her. The status quo was back and again I was hers to use, now don’t get me wrong it was fun and exciting at the time but deep down I wasn’t sure how I felt about it. Especially after some post nut clarity on the many occasions I had to finish myself off after she was done using me.
After some much need vacation time and a trip home, I began to realised how fucked up the situation was. This older woman in a position of power was manipulating, controlling and harassing me to bend and shape me into her personal slave. Looking back now with hindsight it’s clear as day, I was emotionally and mentally in a fragile state after my engagement broke off. Moving to a new city to run from my problems wasn’t the right call and letting my boss sexually harass me in the guise of affection was an escape from my inner turmoils. When I got back to the office I was greeted with an email from her, I knew exactly what she had in mind and choose to ignore her.
She wasn’t happy and her nasty side was back, I began to gather all the evidence I had. Emails, texts, meeting schedules everything I could think of. Again she tired to sneak her way back onto my good side, overly nice and gentle touching here and there. I knew her game now and played along, gathering evidence as I did. Now this next part I’m not proud of and I was contemplating leaving it out all together but the interest of full clarity here it is. Late one evening when the office was empty I spied her having a meeting with her boss, after she was finished I get an email from her asking to meet me in her office. Nothing had happened between us since I realised what she was up to, but I went to her office anyway.
She was back in dominating mode, telling me to crawl towards her. But I had another idea, I lay my cards on the table. Told her I wasn’t going to do anything with her again unless I got something first, after some back and forth she was on her knees sucking my cock. It was lack lustre and unenthusiastically but I didn’t care after almost a year of being teased and denied by her I was in heaven, cumming violently in her mouth without warning as she choked and spat out my cum in disgust. She was pissed off and a very angry telling me to get the fuck out, I then went back to my desk and hit send on the email I had compiled for HR with all the evidence I had against her. What followed was lengthy process of agreements and attempts to cover up and dismiss me, eventually agreeing to a transfer and a rather large hush money settlement. I left the company soon after for bigger and better things.
So looking back yeah I was sexually embarrassed, but I was no better myself in the end. Sure she got away with it and yeah if the sexes had been reversed it would have been national news and I’d be a millionaire with a book and tv deals. But hey I got a nice car and an unhealthy femdom fetish out of it.
Source: reddit.com/r/gonewildstories/comments/va6cwd/my_boss_used_me_as_her_office_sex_slave_mf
Fuck… this runs deep.
How do you feel now you’ve written this out? Any closure?