I really didn't like Kay. She was so nakedly careerist, it was clear she would trample over anyone to make her way to the top, and it was just as clear it was working. She had started with the team just over a year ago, with next to no qualifications or experience relevant our business function but what she did have was confidence and attitude. She would volunteer for every new project or responsibility she could, determined to push herself into the limelight and make sure the management team understood how valuable she was.
Before you think this is just some unreconstructed man who thinks men are being unfairly squeezed out at work by women, I hate this kind of grasping desperate attention to win the favour of management and achieve promotion distasteful in men as well as women. But what really riled me in this situation. Was that I was utterly and completely switched by this woman. Not because she was the most beautiful member of the team (she wasn't in my view), not because she had a red hair (I had always been a sucker for a red haired girl), but because I was besotted with her round soft bum and small firm tits that she knew how to draw attention to just the perfect amount for a workplace.
I would quietly seethe at her efforts in meetings to agree with management, to volunteer of things, or even to announce on world affairs from a political perspective sharply at odds with mine. And then she would catch my eye and smile at me, all the while I would have been thinking about how wonderful it would be to have her nipples between my lips and her breasts cupped in my hand, before I would take her on the meeting room table. Meeting daydreams like this are probably one important reason why I haven't advanced at work like is could have.
As well as ever-determined to succeed she might have been, Kay was also gregarious. She was the one suggesting the team should have lunch together in the break room on a Friday, or go out for drinks on a colleague's birthday. She would keep the conversation going, showing interest in people's lives and bring a playful energy to any social situation. I knew I was wrong for despising Kay but something in me told me that she was going to be trouble and I should keep a wide berth for my own good. It was on one such occasion however that my troubles began.
We had taken a team lunch break on the last Friday of the month and the discussion quickly turned to people's plans for the weekend. Most of the team had talked about their plans for a meal out, meeting up with friends or taking their children to one event or another. I had mentioned how my wife had decided the lounge needed to be redecorated and I had been promising for ages, but now my time had run out! Kay however was true to form when she said she would be spending the weekend studying for her part-time MBA she was doing in her own time, but wished that she had someone like me to boss around and do jobs that needed doing on her house. The team laughed at her audacity and probably at my admission of being hen-pecked at home. But I was just being honest. But I felt I needed to rescue the situation a little so I challenged Kay. A fateful decision.
"So Kay, what do you do when you're not driving your career forward? Do you ever just let your hair down and have fun?" I was being a little catty but masked with a light playful tone.
"I take weak men like you and I make them kiss my ass!" Kay replied with passion, followed by a laugh that the team found infectious. They had taken to Kay's attitude and bravado, and decided they liked watching their cynical colleague taken down a peg.
Feeling on the spot, every one's eyes on me, waiting for my next line, I overstretched. "Ha I would kiss your ass right here and now but I know you don't have the balls for that." I laughed hoping the rest of the team would laugh with me. But instead there was an awkward silence. I had been too defensive and too suggestive, too aggressive. I had lost any sympathy the team may have had and my cheeks began to blush. Kay went for the kill though.
"Ok mister. Let's see who has the balls! Follow me now." She stood up and waited for me to do likewise. The team hollered with the challenge accepted and I quietly gulped to myself, before standing up, not quite believing this would really happen but knowing it would only end with me being humiliated in front of the whole team. Kay had already won but she was driving home her advantage.
"Into the disabled toilet now and lets see who has the balls." And with that Kay turned and headed straight for toilet in the lift lobby. I followed reluctantly behind but was shepherded on my way by the laughs and goading of my colleagues ringing in my ears.
Fuck, was she really going to make me kiss her ass! Or just take this to its logical conclusion and humiliate as being all mouth and trousers in front of the team. As I stepped inside the toilet she closed and locked the door behind me, and I knew both options were still on the table.
"Ok look. I don't like middle aged men like you who think they can take me down in front of the team. I have been dealing with men like you all my working life. So here is how this is going to go. You have a choice. You get on your knees and you kiss my ass until I am completely satisfied you know who is in charge here, or you go back out there and tell everyone you chickened out and that you truly have no balls."
Kay's eyes did not leave mine for a second. She barely blinked. She was deadly serious and she had made that abundantly clear.
"And lets not pretend you haven't been lusting after my ass anyway" Kay added, just to rub extra humiliation into my wounds. My face, feigning shock at the allegation, was transparent and gave me away completely.
"Kay please I think this just escalated really quickly for no reason. Can't we just laugh this off? Look I'll get on my knees and kiss your bum now. Then lets just get back to work shall we.?"
"Oh you can get on your knees alright but kissing my bum does not mean kissing it over my skirt. I mean really kissing my bum. Like you mean it. Like you know that you have been defeated."
Did she mean she was going to let me kiss her on her actual bum, my lips to her cheeks? Oh my god. This was a dream come true, and she thought this was going to be a punishment, a symbol of my defeat? What was she thinking? Did she not know what men are truly like?
"Ha ha yes please!" And at that I dropped to my knees and tried a humorous puckering of my lips in an attempt to lighten the situation and make this feel less of a humiliation.
"Oh no. If you are going to see my bum you are going to be naked. That's a non-negotiable. But on the plus side you get to kiss and look at the bum you have been fantasising about all these months."
I hesitated but I have always been one ready to throw myself head-first into a challenge, usually drinking games at parties, or making silly bets with colleagues that might end with forfeits. And I would be seeing and kissing her bum. So I think we all know what I did next. I started to remove my tie, followed by my shirt and trousers. Kay just watched, her arms folded like a stern headmistress looking over me.
"And those" she said curtly, pointy at my boxers. I was a little nervous now because I knew there was a bit of a semi going on inside these boxer shorts and that would be the most embarrassing part of my predicament. It would show to Kay how correct she was about me lusting after her ass.
But her standing above me in silence and motionless told me that there was to be no negotiation. And this just made the situation inside my shorts even worse. I love a harsh stern headmistress, I'm not going to lie. By the time I managed to pluck up the courage to remove my shorts my cock was almost fully erect and was pointing towards her.
"Good boy." And with that she turned away from me and began to lower her knee length skirt and panties in together in one motion until the waistbands were tucked neatly underneath her bum cheeks.
My dick responded immediately, even faster than my thoughts could to the sight before me. This bum was everything I had imagined it might be and more. So smooth, ever so slightly plump, perfectly round like a peach, and the slightest hint of a wobble. Clearly Kay put time in on this ass at the gym, but not so much that it detracted from its natural feminine form.
"OK people, he's going in for his first kiss of my ass!" Kay said in a loud voice so the ears of those stood open the other side of the door could hear. They laughed and cheered their approval, reminding me of their presence and how I had needed up in the situation due to their enjoyment of me being taken down by Kay.
Kay pushed out her bum just a little, to make it obvious she was ready for the first kiss. I wasted no time planting a big puckered kiss on Kay's bum cheek. I pressed deep into the soft pillow, until my nose touched her cheek also, when I could enjoy the scent of a floral soap lingering on her skin.
"That was one cheek. Now the other." Again in a loud voice so colleagues outside could hear, once again met by cheers.
I did as I was told. I was all too happy to. Again, it was a firm and lingering kiss. I really didn't want my lips to leave her cheek. But Kay decided enough was enough and she straightened up and turned round.
"I'm glad to announce he does have some balls after all." Kay said as she pulled up her skirt and panties to their rightful position, with colleagues cheering once again.
"See, that wasn't so bad was it? Remember next time though that if you piss me off again I will break you in a way you will never recover from." Kay had almost spat those words at me in a harsh whisper..
"Ok im sorry I was just playing around." I tried as an apology.
"You were trying to bring me down a peg or two with your colleagues but you feel threatened by me. I know your type. But its ok, you are lucky and you submitted to me and kissed my ass. We both know where we stand now."
"I did not submit to you" I replied, now trying to regain some dignity by putting my clothes back on and standing up from my knees. "All I did was kiss a cute ass."
"Oh you submitted - and you will do it again whenever I tell to you too."
"Ha ha I don't think so Kay. You've had your fun, your little victory but this is never happening again."
"Oh you fool. Where's your phone?"
