Flash Fiction Friday – The Pleaser

This Flash Fiction piece has been inspired by a conversation I had with a man only known as The Pleaser. 

The Self Pleaser

I was bored out of my mind. While my boss droned on about new ways to improve productivity on the workfloor, I drew doodles on my notepad. My phone was on mute. I had decided to work from home today, but that was before I realised we had a two hour long conference call. And there was no way to skip it. Luckily I had had the presence of mind to plug in my earpiece, so I had my hands free.

I slouched on the couch, half an eye on my computer screen. I had seen this presentation three times now and it didn’t improve on repeat. I wished I was in the office, at least then I had Callie to play footsie with. The things that woman could do under the conference table without our boss noticing was amazing. But now I was stuck at home dreaming of her foot slowly rubbing my cock through my trousers.

I shifted on the couch. Just the thought of Callie made me growing with desire. Man, if she were here I could think of a much better way to spend our time. She had once hinted at the things she could do to me in bed – or even out of bed for that matter – and it left my imagination running wild. It didn’t help that she was hot – big breasts and the perfect ass. I had heard her complain to a colleague that she thought she was too fat, but she was perfect in my eyes. I would not say no to that ass grinding my cock.

As my boss droned on, I had a sudden thought. I was alone, at home, with my phone on mute. It was not likely that my boss would ask me any questions, I was just there to be another bum on the seat – or a person on the phone in this case. I unbuttoned my jeans and took out my cock. It sprang free, almost fully erect. I closed my eyes and imagined Callie naked, her breasts pushed in my face, her hips lowered on my lap, my cock buried deep inside her. I began stroking my cock, slowly at first, pre-come dripping from the tip. I teased myself, prolonging the build up to ensure a greater release at the end.

‘As John would say…’ At the sound of her voice, breathy in my ear, my eyes snapped open. I had been so caught up in the fantasy I thought she was really there. But she was merely starting her part of the presentation. It could not be better. The sound of her voice drove me wild, despite the boring subject. I moved my hand in earnest now, stroking hard and fast. My climax built, threatening to take me over the edge. I considered pulling myself away from the edge, but Callie spurned me on, and with one last stroke – and the image of Callie arching her back in climax with me – I came. My hot cum flowed over my hand and I slumped back on the couch, breathless from the glorious relief.

‘Maybe John can say a few last words in closing,’ Callie said over the phone.

I fumbled to unmute my phone, took a deep breath to steady myself and spoke my closing remarks. The timing could not have been better. It was a good thing I knew the presentation off by heart.

I hoped one of these days I could make my fantasy a reality.

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