tagFetishJill Gains The Upper Hand Ch. 01

Jill Gains The Upper Hand Ch. 01


I live on my own at the moment. I'm an avid reader and recently began reading one of P G Wodehouse's stories. He's such a good writer and very funny. But the more I read about Bertie Wooster and his butler Jeeves the more I thought how nice it would be to have a Jeeves of my own. Obviously such people no longer exist (if they ever did) but I thought if I could train a boyfriend to do it, he would be the next best thing.

I'm always attracted to the strong masculine males but they are just the sort who expect their partners to wait on them rather than the other way round. I've had some good fun with various men friends but as soon as they move in with me the arguments start. It's fine early on as they always want to pay in restaurants, which I quite enjoy. I call that "the courting stage" when we're both on our best behaviour but many of my relationships have not got much further than that. I'm thirty-five now and ready to settle down with a guy, maybe have kids with him. I've been doing a bit of research on the internet and am encouraged to learn that there are a lot of men out there who secretly desire to serve their partner even though their demeanour and behaviour give out the opposite impression.

At the moment I'm not working but it's not a problem. I used to work in the city of London. I was a high flyer but the job did not work out and I ended up with a very generous redundancy package. It might be nice to find an easier job for a while, one that doesn't involve such a long commute. In reality I don't need to work for a year or two but I like to have structure in my life and a job provides that.

I'm looking through the job vacancies in our local paper when I spot an ad with the photo of the managing director staring out at me. He's handsome, (a bit like Paul Newman in his younger days) and requires applications from persons who have trained in shorthand with good IT skills to work in his admin department.

I do know a bit of shorthand from my days in journalism so I arrange to go in for an interview.

"Aren't you going to test my shorthand?" I ask Mike Nelson, the Managing Director. This is a very strange interview I'm thinking. He's talking after only a few minutes as if he's already decided to take me on.

"That won't be necessary Miss Martin. The truth is you may not need it. It sometimes helps taking down long messages over the phone but I always think that putting it in the advert ensures a better class of applicant and someone of more mature years. I'm not allowed to specify gender when I'm seeking new staff but I wanted all the applicants to be female. I can see from your CV that your IT credentials are first class."

We talk through salary and working conditions and he gives out a strong hint that after a time I could work from home for up to two days a week, which I'd love to be able to do. He's very charming and attractive. I can see he has an eye for the ladies and he begins to flirt with me once I have agreed to take the job. I find myself responding in kind but only let it go so far, this is neither the time nor the place. I am strongly attracted to him, he's the kind of man I've dated before but I am determined to hold back this time. I'm still looking for my Jeeves type partner.

I've only worked there a few weeks when the other female staff put me wise to Mike.

"He's still single and some people describe him as a confirmed bachelor but he likes women, plural." Says one.

"He's not averse to going out with members of his staff but he's quite picky. They have to be lookers. So watch out, you won't be immune." Says another.

I'm flattered by that comment. Mike has already come on to me but I'm playing it cool. "Treat 'em mean, keep 'em keen" is my new motto. I also need a plan if I'm going to gain the upper hand. Then I learn how competitive he is. He plays squash in a league and competes in orienteering events. There are details of his successes on a notice board in the staff room and he even has a cabinet in his office with one or two trophies. He's in a quiz team that's top of the league and has recently joined a local chess club. That gives me an idea.

The next time he suggests taking me for a meal I accept. He's good company and we have a lot in common. Pretty soon we are out together every week. I'm driving him wild, permitting a bit of fumbling, hot kisses, cheek to cheek dancing but keeping him out of my panties. We've been swimming together so I've had a good look at his body. Nearly six feet tall, broad shouldered, not an ounce of fat on him. I don't like body builders, they seem unnatural, but he has the perfect body for me. I want him but am managing to keep to my plan. To take the edge off my cravings I've updated my vibrators, the rabbit one brings me off the quickest. But I don't need to search the internet for erotica, old pictures of Paul Newman and imagining sex with Mike is quite enough to get me going. Mike has those same striking blue eyes and when we make eye contact my legs turn to jelly.

One night after another lovely meal and some dancing he drops me off at my flat and we kiss in the car. This time the kiss is long and lingering with our tongues searching each others mouths as lovers tongues sometimes do. I allow myself to moan a little and suggest he comes inside for coffee, breaking off our clinch as he begins moving his hand up the inside of my leg. Once inside we waste no time, undressing each other quickly. I drag him into the bedroom and abandon myself to my desires. He does not disappoint. Mike stays the night.

"I noticed the chess set in the living room, Jill." Mike says as he munches cornflakes next morning. "Do you play?"

"Hardly ever these days. I like to keep the pieces set up like that more as a kind of ornament. Why do you ask?"

"Well er, I'm in a chess club. Maybe we could have a game some time."

"I'd like that. Okay, how about tonight. You could come for a meal here and we could play after. It's about time I cooked for a change."

Mike beams. He's not the type to move on to the next woman once he's had his wicked way with them.

What Mike doesn't know is that I used to play chess with my dad every day as a child. Dad was very good but eventually I began to beat him and we stopped playing after that; something to do with the male ego.

I let him win the first game. He lets me win the second.

Later that evening after we've had our meal; "What about making the games more interesting next time we play?" I says this casually with an impish grin. "We could make the other person do something they don't want to do if they lose. What do you think Mike?"

They are lying in bed together side by side watching TV. Mike reaches for the remote and turns off the TV. He gives me a brief kiss on the lips.

"What did you have in mind, darling?"

"How about if I win the next game you do all my ironing for a week wearing nothing but an apron? I'd like to see that."

"Okay," he says laughing. He clearly believes it will never happen. "And you could agree to wear a dress or a skirt for a week. You're always in trousers or jeans."

"That's too easy dear, tell you what, I'll wear a skirt for a week if you win- and shave my pubes- and go without panties. How does that sound?" My face reddens but I manage to hold his gaze, watching his eyebrows go up and his mouth fall open.

He grabs my hand and shakes it. "You're on! See what you've done to me." Mike pulls back the covers and reveals a stonking hard on. I reach across and begin stroking him.

"Think of me dear, at work every day in the office, wearing dark hold up stockings. You pass my desk knowing I'm hiding a hairless, pantyless quim between my legs. You call me into your office just to check and I pull my skirt up around my waist for you to see my cunt glistening with moisture as I enjoy the horny feelings going bare arsed gives me. You'd like that darling wouldn't you?"

My pace quickens. "Oh, Yes, Yes." He says as his penis erupts all over the bed.

"Why don't you lick me whilst you think about how smooth my pussy will be if you beat me at chess."

I wasn't sure if this was a step too far at this stage. Maybe because we are still in "courting" mode, Mike moves quickly down the bed to complete the task I have set him without saying a word. He's good at it and soon has me screaming out as a very satisfying orgasm wracks my body.

"Thank you dear, that was delightful." I yawn and turn my back to him with a satisfied sigh. I know he wants more and can feel his erection as he spoons me. I'm ready to go again too but pretend to be fully satisfied.

"Goodnight sweetheart, I need to get my beauty sleep."



As soon as I meet Jill I know she is a cut above the rest. I'd read her CV carefully before the interview wondering why she is interested in doing a job which is so well below her capabilities. She's quite honest about her reasons from the start. I'm happy to employ her even for a short time until her redundancy money begins to dwindle. I also want to get her into bed and bringing her into the firm improves my chances.

There's something about Jill that I can't put my finger on. She's so confident and self possessed but it's not just that. It's like seeing me is very important to her so she wants it to be right. A bit like a game where I don't know the rules. I'm in my mid thirties, enjoy the single lifestyle, but over the last year it's lost some of its sparkle.

That first time when I'm in her flat and in her bed is awesome. Then she comes up with the bet. As we talk it through in bed one evening the idea of Jill paying a sexy forfeit gets me hard. I'm a winner at most things and am sure she's got no chance when it comes to chess. I play every week for god's sake.

The trick is to think three or more moves ahead, at the same time forcing your opponent onto the defensive. But Jill is good. When I take her queen I'm confident of winning but three more moves and she's check mated me. What a shock!

"Please Jill, make it best out of three. I must have lost my concentration for a second."

I hate to lose and my face is burning with shame. Blood has also gone to my penis and I readjust my trousers hoping Jill has not noticed.

"A bet is a bet. You agreed to this."

"I know, can't we increased the stakes a bit? Please make it best out of three. I'll do your ironing for two weeks if you win."

Jill points to the ironing pile.

"I've been saving it up. I want every item neatly ironed. Strip off, you can start right now." She brings me one of her aprons from the kitchen.

This isn't what I had in mind but as I take off my clothes there is undoubtedly a sexual thrill. I've never told anyone about looking at femdom sites on the Internet but the evidence that I'm turned on by this kind of thing is there for Jill to see.

"Wow Mikey boy that's quite a stiffy you've got there. I wonder what it is that's got you so excited."

I don't even do my own ironing and as I stand in front of the ironing board my face reddens. I'm used to being the winner but accept that she beat me fair and square so there's nothing for it but for me to carry out my forfeit. I'm embarrassed and humiliated but I'm forced to recognise, (a hard pill to swallow), that my cock is as stiff as it's ever been. I'm the one who calls the shots. So why does serving Jill excite me so much? I can't let her know how much I'm getting off on this.

It doesn't take me long to get to grips with the nuts and bolts of ironing. Jill is quite attentive this first night and I can see that she too is turned on by my predicament.

"Make sure you keep the iron topped up with water darling. It's the steam that does most of the work. You'll soon get the hang of it." She pats me firmly on the bum and I accept it without a word. I try my best to look unhappy, determined to conceal from her the extent of my enjoyment but my penis continues to stand up despite my desperate attempts to make it go limp. It seems that the more humiliated I feel, the stiffer I get. Jill suggests that I stay at her flat for the week of the forfeit and I agree. She takes a couple of photos with her digital camera.

"It's okay, don't worry I'm not going to post them on Facebook dear. These are for my own personal use."

I toil my way through the ironing pile until I've completed about two thirds of it. It's a hot evening and I'm warm even though I'm without clothing.

"You can leave the rest until tomorrow. It might be nice to have an early night for a change. What do you think dear?"

I switch off the iron, take her hand and drag Jill into the bedroom without answering. She has a king size bed with the headboard against the far wall. I roughly swing her round so that she flops forward onto the bed with her feet on the floor, then quickly pull her jeans and panties down around her ankles. Without preamble I push myself into her from behind. She's so wet that I'm up to the hilt immediately. Jill grunts but makes no complaint as my cock drives home and I begin to push in and out holding on to her breasts tightly through her clothing. It's as if I'm trying to reclaim my manly persona again. Jill urges me on.

"That's it Mikey boy, let me have it. I love to feel your little pole worming its way into me. Watching you iron has made me wet."

Little pole? Is she trying to say that I have a small penis? No way. And yet, once again I feel that surge of embarrassment and humiliation, coupled with increased arousal and it isn't long before I spurt. Shouldn't I challenge her comment? My emotions are in turmoil and I don't feel up to arguing so decide to leave it. There are six more days of this. How am I going to cope? Later in bed Jill complains that she didn't orgasm earlier. I don't offer to go down on her this time so she strokes me to an erection, puts me on my back then lowers herself on to it, soon bouncing up and down above me. I've done this before but this time I find it a lot more satisfying.

At work during the day I try very hard to regain the initiative. I am the boss after all but I'm paranoid that something of what is going on will get around the office so I daren't order her around and tick her off if she makes errors. She's respectful in front of the other staff but behind their backs she is winking at me and grinning, casually talking about my task tonight as if I would forget.

It's obvious Jill is maximising the amount of ironing available for me every evening but there is a limit and once that initial ironing pile is done the work eases off and I spend less than an hour each night stood in front of the ironing board. I do have to miss chess club though so the two of us play a few games instead. I finally realise what a good player she is. It's such a struggle acknowledging her superiority and makes me re-evaluate the way I see women. She wins every game. At least I'm learning better chess strategy. After that first night Jill leaves me to do the ironing whilst she reads sitting nearby on the sofa. There is always a sexually charged atmosphere and we make love every night in her bed.

I complete the seven days with mixed feelings almost wishing I could carry on ironing for Jill. She thanks me and gives me a big hug and a kiss when the final item is ironed.

"There, it wasn't so bad was it? You must have realised by now that I set you up. It was a kind of test. You passed it with flying colours. I like you very much but am really looking for a man who is willing to be in a Female Led Relationship or FLR. I have a feeling that you are that man but that you find it impossible to admit to it--- even to yourself." Jill stares into my eyes and I look away.

"I can see that I'm going about this all wrong. Will you promise me one thing? Will you look up FLRs on the internet?"

This is a lot to take in. I nod my head unable to speak. This is not the time to reveal to Jill that I am already fully aware of what an FLR is. I've found the usual fem dom sites with their whips and penis torture a bit of a turn off. Increasingly when searching for masturbation material on the internet it is the psychological behaviour of powerful women that has worked the best. I use those stories and they work for me but I am always disturbed afterwards. Why should behaving like a wimp around women get me so aroused?

We are both busy for a couple of days so agree to meet up for a meal on the following Friday night. Back in my own flat I start brooding about what Jill has just said. I realise that I've become very close to Jill and learned a lot about her over the last week. I've seen her cry over a drama on TV that we watched together. She said it triggered a memory about her father's death from a heart attack when he was only fifty. We talked it through together and it was interesting that she was not afraid to show her vulnerability. He was the guy who taught her chess apparently. I've started developing feelings for her so don't want to end the relationship. But surely an FLR is not for me. Surely not! Maybe we can carry on seeing each other without me agreeing to anything like that.

We continue dating over the next two months. There is no further talk of FLRs but I realise that Jill is making most of the decisions and it feels okay. I'm in the habit of staying at hers at weekends and the sex is great. There's just been one thing that's been troubling me.

"Jill? You know that week when I stayed at your house?"

"How could I ever forget it dear. We had some good fun didn't we?"

"You mean you did. Okay, sorry, maybe we both did in a way. You made a comment about the size of, the size of mmmy....."

"Your cock. Okay, what of it?" Jill looks me straight in the eye and smiles.

"You've had loads of other boyfriends in the past I suppose?"

"Yeah, why?"

"Well were they all, I mean, well, er, were they all more er, well endowed than me?"

"Well some were bigger and some were smaller. Does that answer your question?"

I nod. I want to ask her if she likes bigger cocks but can't bring myself to say it.

Sometimes she's not feeling like letting me go inside her but on those occasions she will take me in hand, saying all sorts of dirty things to get me going.

One Saturday night about two months after we first met she's wanking me as we lie in bed but keeps stopping as I'm reaching my climax.

"How much do you want to come darling?"

"Please don't torment me, you know how much, please let me come, please, I'll do anything."

"Anything? Well. Well, let me think. From now on you will call me Princess whenever we are alone. Is that clear? I don't want to hear Jill from your mouth unless maybe there's another person within earshot."

"Okay Princess, I promise, now let me come, please."

"Right my little Mikey boy, you want to please me don't you? You'll do anything for your Princess won't you dear? Her hand moves faster and faster.

As I nod my head in agreement and say "Yes Princess, yes," I shoot my load into the tissue she is holding realising that this is one of my strongest climaxes ever.

The next day, back at my flat I feel a bit strange. Jill is slowly taking over the reins of this relationship and I feel powerless to stop it. It's a turn on sexually without a doubt but the alpha male in me is resisting. Jill and I have no plans this evening so I decide to ring around a few of my mates and arrange a night out at the pub.

It's short notice so only three turn up. Two are friends I went to school with and the third is Mary who I studied with at University. Tom and Jim are both married with kids so they don't stay for long although we drink fast and polish off quite a few pints whilst they're there. It's a warm evening and we don't want more alcohol so Mary and I take a stroll together.

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byQuietoldie© 12 comments/ 32017 views/ 14 favorites

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