Anal Appraisal

By Jake Summers

Published on Feb 26, 2019

Gay

Controls

================================================================== [Disclaimer: This is a work of fiction. Any similarities between actual events and the events in this story are purely coincidental. Any similarity between actual persons alive or dead and the characters in this story are purely coincidental. This story involves descriptions of risky sexual acts between men for the purpose of erotic fantasy, and as such is not intended to condone such acts. If you are underage, or homoerotic material is otherwise illegal where you are, please do not continue. The author retains copyright; do not duplicate or use this story in any way without the author's explicit written consent.

Comments and suggestions are welcomed by the author at jakeonhisknees@gmail.com.] ==================================================================

Anal Appraisal - Part 1

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From: STEWART Richard richard.stewart@stewartstrategy.co.uk Sent: 12 April 2019 16:37 To: SUMMERS Jake jake.summers@stewartstrategy.co.uk Subject: Meeting this afternoon

Hi Jake,

Sorry to grab you last thing on a Friday, but could you come to my office for a short meeting before you leave? Thanks.

Rich

==================================================================

From: SUMMERS Jake jake.summers@stewardstrategy.co.uk Sent: 12 April 2019 16:44 To: STEWART Richard richard.stewart@stewartstrategy.co.uk Subject: RE: Meeting this afternoon

Hi Richard,

Certainly, no problem. See you at 5:30.

Best,

Jake

==================================================================

I send the reply, frowning. This is unusual. I don't normally hear personally from Richard much, since he's the director and I'm just admin. I worry what it might be about. I'll be doing my annual appraisal with him next week, it could be to do with that. For the next 20 minutes, having already mentally clocked out, I mess about on social media, waiting for the time to pass, watching everyone else leave. Then I switch off my computer, pick up my rucksack and head downstairs to Richard's office. I knock on the door and let myself in.

Richard is behind his desk, working at his computer. He's turned sideways and doesn't look round when I enter, just says brightly but distractedly,

`Hi Jake, take a seat, I'll just be a minute.'

I sit across the desk from him, putting my stuff on the floor to one side. As he continues typing, I notice he has a photo of him with his wife and daughter on his desk. Richard is pretty hot (in the picture, as well as in front of me right now) and I've always felt a bit bashful in front of him because of that. He's maybe 40 or 41, with dark, shaved hair and short, tidy black stubble with some flecks of grey. He's got a bit of a Mediterranean look about him: tanned skin, a slightly rounded face, large brown eyes, full lips. He's wearing a light blue shirt with a purple tie, slightly loosened. I reckon he probably used to be muscular but has gone a little bit soft through fatherhood. I'm just taking all this in when he finishes with his computer and turns to me.

`Hi, Jake, sorry about that. Yes, so, I just wanted to have a word with you about something.'

`Oh, OK. Is it...related to my annual appraisal?' He gives a short laugh and shakes his head.

`No, no, nothing like that. Eh, this is about...pleasure, not business.'

I know there's a bemused expression on my face. My stomach tightens and my heart skips a beat. What does that mean? He smiles at my confusion, and turns his monitor around so I can read what's on it. It's the Sent Items folder in his emails. An email is visible, sent a few days ago. I read.

==================================================================

From: STEWART Richard richard.stewart@stewartstrategy.co.uk Sent: 9 April 2019 21:47 To: 47 recipients || [Show all] Subject: CONFIDENTIAL: Annual bonus.

Hi guys,

As discussed at your recent annual appraisals, I have organised a reward for you all as a thank-you for working so hard this year. I know many of you have troubles with the missus' from time to time and/or maybe don't get to relieve yourself' the way you would like, as often as you'd like.

To remedy this I will make a willing slut available for use in the disabled toilet on the second floor, this Saturday 14 April between 12pm and 5pm. There is no limit to what you can do to him, provided there are no visible marks on him when he comes in to work on Monday morning. Condoms will not be provided so bring your own if you prefer - but if you're anything like me, you won't want to use one anyway.

A friendly reminder: this email should be considered sensitive and confidential. The slut is a service to only you, and what happens in that toilet is your business.

Enjoy.

All the best,

Rich

Richard Stewart Director Stewart Strategy

==================================================================

As I read, I try to control my expression but I feel like my eyes are getting wider and wider. Once I'm done, I look over at him. He's leaning on his right elbow, stroking the side of his head with one finger and looking right at me, a bit of amusement in his face. I put my eyes back on the monitor so as not to meet his gaze, and I wonder how I'm going to stand up given how hard I suddenly am. Time stretches out as I wait to see if he's going to offer any explanation. When he doesn't, I clear my throat, drag my eyes to his face and say,

`Um. I. Is this...something you're inviting me to?'

He doesn't answer. After a moment I continue.

`I don't think I got that email...'

He laughs softly, and playfully says,

`Why do you think that might be?'

I notice that his shoulder is moving up and down. I follow the line of his arm to his elbow, to where it goes under the table towards his groin, to where it's moving slowly and rhythmically.

`Stand up and come round here.'

I'm stunned.

`I...sorry?'

I said, come round here.'

His arm is still moving. His eyes follow me as I stand up, and as I move round to his side of the desk he swivels in his desk chair, so that by the time I'm standing next to him, I can see that he is rubbing the long, thick tube of his dick through his dark blue suit trousers. The trousers are well fitted, so I can see that it's aimed towards his left hip, throbbing under his palm.

`Get on your knees.'

He has a smirk on his face as I get down on my knees. He slides his chair forward until I'm between his legs. He reaches out with the hand that was rubbing his cock, puts it behind my head, and firmly pulls me face-first into his crotch of his trousers, holding me there.

I take deep breaths through my nose. I can smell a faded scent of detergent, which must be the trousers. Beneath that, I can smell a warm, heavy, manly smell, and an underlying acrid note of sweat of a day's rushing from meeting to meeting. I can feel the strength and hardness of his knob against my face, and the incredible heat radiating from it through the crotch of his trousers.

He pushes me away and I sit back a bit. Not taking his eyes off me, he pulls his zip down, slides his hand in, fishes his dick out of his underwear and through his zip. As he does so his thick foreskin slides back a bit exposing the deep purplish head of his cock to the air. It's slightly wet with precum, and a very different colour from the darker skin of his shaft. He leans back in the chair, arching his back, letting it jut out to a full, thick eight inches, before putting his hand behind my head and pulling me down towards it.

Dimly, I smell the dull tang of dried piss and semi-dried precum from his head as he slides it into my mouth, guiding me down until his glans makes contact with the back of my mouth. I hear him give a shaky breath, and he begins to pump his hips, thrusting shallowly up into my mouth with his left hand still on the back of my head. I groan as he fucks my mouth, my hands braced on his powerful legs.

Then he's trying to push deeper into my throat, pushing up with his hips and down on my back with his left hand. He moves his right hand to lightly hold my throat. Then, the angle improved, he edges his hips forward and slides slowly into my gullet.

My eyes water as he holds his cock there. His foreskin has peeled back from the big sensitive knob, around which I now reflexively swallow, eliciting a short, sharp gasp. His hands around my throat flex and I feel his fat dick throb along my tongue. After a few seconds he seems to manage to calm down, and starts to rock his hips, giving slow, deep thrusts in and out. I can feel at the back of my tongue that each time he withdraws a bit, his foreskin is rolling some way up and over his glans, and when he pushes in the foreskin peels completely back and his bell end stretches my throat again.

Precum is seeping continuously into my boxers as he holds me in place and uses my throat. I can hear him giving low, gruff moans in between deep, calm breaths. These get louder and more ragged as his knob gets bigger and thicker, and his big balls are getting tight against my chin.

I swallow around him and realise that I can taste sweet-salty precum in my mouth and feel its thick stickiness in my throat. All of a sudden he pushes deep and freezes, his hands flexing around my throat again. He makes a sound like he's taking in a slow breath through gritted teeth, which makes my own dick strain against the fly of my jeans. I can feel his balls are tight, and his shaft and cock head are rhythmically tightening and releasing, the swelling stretching me out and threatening to make me gag; he's close.

He doesn't, though. He lets out his held breath slowly, and as he does so he loosens his grip on me and smoothly slides out of my throat and mouth. I realise I've been holding my breath too, and it comes out in a rush, before a series of deep panting moans as I steady myself on my hands. My mouth is full of the rich taste of his precum, and I get a sharp flash of flavour as I swallow several thick gobs of semen he'd dribbled when he was on the edge.

`I'm gonna keep that for tomorrow,' I hear him announce mildly, and then the rustling of him tucking himself away and zipping up.

Catching my breath, I get shakily to my feet and move round to the other side of the desk to collect my rucksack. As I do, he gives a soft but not unfriendly laugh. I look over to him, feeling weirdly shy about meeting his eyes. He just looks at me for a moment, then says,

`So. See you tomorrow at half eleven?' He gives a wicked grin, flashing tidy white teeth.

I haven't a clue what he means. I'm thinking that if he looks down he'll see my cock hard in my jeans and a dark spot where I've been precumming, as if that matters now. Then I remember. It takes me a couple of tries to get the words out, which don't seem to be connected to anything happening in my brain.

`Oh, uh. Yeah. Yes. I mean, I'll be there.'

He smirks again.

`Good. See you then.'

Just like that, he turns back to his computer, taps the space bar a couple of times to wake the screens up, and goes back to typing. I open the door and stagger out in a daze, wondering what the fuck just happened, and what might be coming tomorrow...

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