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Sucking My Boss

Category: Gay Male
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My boss Justin wasn’t a beautiful man. He was short with a badly trimmed moustache, a thatch of white hair, huge sweet patched under his armpits & rather a large beer belly. But he was my boss so I treated him with a certain amount of respect. After a few too many glasses of champagne at the Christmas party I’d let it slip that before I’d married my wife I had in fact had a boyfriend.

It wasn’t exactly a secret. My wife & my friends knew all about my past. However it wasn’t something that I wanted to discuss with my colleagues at the conservative finance company.

So, it was with trepidation at I sat across the desk from him in my first performance review. “Well, that’s great. Thanks Dillon. You do good work.” He paused but made no move that would indicate he was done talking to me. “So you’re not married, right Dillon?”

“Yeah, Krystal & I got married in February. It’s been almost twelve months now,” I answered softly, wondering where this was heading.

“Oh yeah. That was just after you started working here. No kids, Right? “He said with a nervous laugh. I knew that Justin was married and had three young children. He was about forty and I’d seen his wife a number of times in the office and at social functions. She was attractive and pleasant but not an overly friendly person. “After the third kid, things just haven’t been the same between Julia and I. We put up a good front but I haven’t been too happy with things for a few years now.” I wondered why he was spilling his guts to me about this stuff but I sat patiently and nodded in agreement where it seemed appropriate.

He noticed my hesitation and said, “Would you join me for a drink? I think this situation is a little stressful for both of us.” He uncrossed his legs to stand, and in the process his foot brushed the side of my leg nearest to him, he said “Oh, sorry, I didn’t mean to kick you,” he said as he patted my shoulder as he moved over to the set of drawers a few meters away.

“That’s ok, I’m not fragile.” I said as I started to get up and follow him.

“Don’t get up,” he said, “We’ll need the table for some things I want to show you.”

I stayed seated but swivelled in the chair so I could see him without twisting my neck. His tone was neutral, but I wondered if what he wanted to show me was a letter of termination.

“I’m having Bourbon. What can I get you?” He asked as he poured just a splash into a tumbler.

“That’s good for me too, but I’m somewhat of a lightweight when it comes to the hard stuff.” I answered.

He ignored my “light weight” comment and poured two fingers into another tumbler, came back to the desk and handed it to me. “To the enjoyment of life!” he said as he raised his glass to me. I raised mine to clink his, and then took a swig, thinking to myself it was odd to offer me a drink, and odd to make such a lame toast while deciding if he was going to fire me. And I noticed he merely sipped his drink.

He set his glass on the table

“You mentioned at the Christmas party that you had been with a man before you were married?” he said nervously.

“Ummm….yeah….I guess.” I wasn’t sure how to respond. This was totally inappropriate. Whilst I didn’t want to get into any trouble but I didn’t want to lie to him either.

“How long ago?” he asked with a curious tone to his voice.

“a few years,” I looked down and felt my face turning red with embarrassment.

“did you have a boyfriend?”

“Not really, no” I said with a shrug of my shoulders.

“So if you didn’t have a boyfriend…..what kind of relationship did you have?”

“He…uh….well…he….uh…well friends with benefits mainly. And there was a guy who liked me to service him,” I stammered as I looked down at the floor, ashamed of myself.

“Service him? You mean, like, you suck him off when he wants you to?”

“Yeah, I guess. And other stuff.”

“Other stuff…… what?”

“Well, sometimes he fucked me and sometimes I licked his asshole.”

“Holy shit! You’re kidding me?!”

“No sir.” I don’t know why I called him “Sir”. We had a very relaxed office atmosphere and only referred to our supervisors by their first names.

“Sir, eh?” Justin said and paused as he fixed me with his gaze. “I’m going to be brutally honest with you Dillon. It’s been a couple of years since Julia and I have had any kind of sex and she hasn’t given me head since the first kid was born years ago. Ever since you made that one off comment at the Christmas party, I just can’t get those images out of my head. They made me really fucking horny and I can’t stop thinking about you with cum all over your face. So….well…here it is….could I ask you to do me a favour and suck me off?” His words came rushing out of him as he seemed to finally get up the nerve to get his feelings off his chest. I looked up at him and could see both the anxiety and nervousness on his face.

I was shocked.

I was disgusted.

But above all I was excited.

“Yes, I would love to do that, Justin.”

“Okay, great!” he said and it looked like a wave of relief washed over him. “Go lock the door and then come over here,” he said as he turned his chair sideways from his desk. I went to the door and clicked the lock. When I turned around, Justin was standing next to his chair. He had kicked off his shoes and was undoing his belt as I walked towards him around the desk.

“Here, let me do that for you,” I said as I dropped to my knees in front of him. With my face inches from his crotch, I undid his belt, opened the top tab of his pants and slid down his zipper. I pulled his pants down and helped him step out of them. I was confronted with a bulge tightly encased in a pair of maroon & green striped undies. I slowly stroked my palm across the grey hairs that covered his belly. As I got closer to his dick I just couldn’t help but cup his bulge. He got stiff rather quickly so I continued, firming my grip and squeezing his balls in my palm. I could feel the heat of his hard cock right thru his undies.

I started to pull down his underwear, exposing his dick. It wasn’t all that big, a little smaller than average I guess. I was surprised at how hard his cock got in such a small space of time. I looked down to see his purple knob head, shiny and smooth, staring up at me from the thick foreskin, that I rolled back & forth across it as my hand jostled back and forth across his shaft.

I don’t have a foreskin myself so the novelty was rather fun.

“Do you think it’s too big? Do you think you’ll be able to suck it okay?” he asked. Obviously Justin was seriously delusional about the size of his tackle. But I had no intention of bursting his bubble.

“It’s not too big…it’s just perfect. And I’ll think you’re gunna like the way I suck it. Now just sit back and let me do all the work,” I said as I pushed back on his jelly belly. He dropped into the chair and I crawled forward between his spread thighs. I pushed the tails of his shirt to each side to give me free access to his rearing cock. I reached my hand around his girth and pulled his rampant erection down until it pointed directly towards my lips. I gripped the base of his shaft tightly and milked it firmly forwards as a glistening drop of precum appeared at the gaping eye. I could see that he was already starting to breathe heavy. Just before I slipped my lips over his engorged cockhead, I looked up at him with pleading eyes.

“I hope you won’t think bad of me if I swallow your cum, Justin,” I said as I reached out with the tip of my tongue and slid it around the drooling tip.

“Oh fuck no! I’d love for you to do that,” he said with a glazed look in his eyes. “Oh shit, that feels so fucking good,” he exclaimed as I slid my lips past his thick corona and bathed the throbbing knob with my salivating tongue. I moaned loudly into the velvety soft membranes and then slid my head further down his shaft.

“OH FUCK…..OH…..OH……AAAAAAHHHH,” he bellowed as his cum started to spew into my mouth. I was initially shocked by how quickly he came but then I remembered him talking about his recent history and he must have been so turned on by the whole experience. I felt the first blast slam against the roof of my mouth and then locked my lips on the head as it kept erupting into my mouth. I pumped my hand furiously on his throbbing rod as it spasmed and continued to unload relentlessly into my waiting mouth. It tasted wonderful, strong and manly as if he had it stored up for a long time. I kept as much in my mouth as I could and I could feel some start to leak out the corners of my lips as he just kept shooting and shooting. His moans of ecstasy were a delight to my ears and I kept sucking as I tried to coax as much cum out of Justin as I could. His climax had his legs twitching and he was bucking his hips up into my eager mouth. He finally slumped in the chair and his ragged deep breaths signalled me that his orgasm had finally finished.

“Oh my God,” he said. “That felt incredible. I’m sorry it happened so fast. Did you swallow it?”

I nodded.

“Dillon, that was fucking amazing. I didn’t ever think I would like it with a guy like this.” He paused for a second and then looked down at me. “Ummmm……..I think I can cum again, But first can I return the favour, if that’s okay with you?” he asked timidly.

“That’s fine” I said with a smile.

“Well” for a start you are wearing too many clothes…” he said with a smile.

I stood up and quickly discarded my tie and shoes. Next I unbuttoned my shirt and my trousers and undies were around my ankles in one swift movement, exposing my erect cock. He watched it seeing the drip of precum on its tip and touched it with his finger and lifted it to his lips. There was a quick flicker of smile as took my cock into his hand. Slowly and gently he began to stroke the flesh up and down. While he did this I reached between his legs to take his semi-erect cock into my hand and I began to mirror his stroking.

He moved closer to me and we propped our bodies into semi-reclining positions so that we could play and pleasure each other. My cock was bigger than his, both in length & girth but neither of us mentioned the fact.

“Are you having fun?” I asked.

He smiled and spat on his hand so that he could pump his podgy little hand slowly on my cock. Standing so close to him he seemed to fill my whole vision. His scent filled my nose, a combination of body odour and the musk of excited man-flesh.

“Oh please Dillon. I’ve got to cum,” he pleaded. Dropped to my knees and took him into my mouth again. I plunged my face forwards taking him balls deep into my throat again and again as I sucked him I took my fingernails and dug them into the flesh of his arse.

“OH FUCK…..THAT’S SO GOOD…..FUCK….HERE IT COMES!” he shouted as I felt the big vein on the underside of his cock start to pulse. I pulled back just in time as he started to flood my mouth once again. I savoured his musky manly taste on my tongue as the creamy wads of his semen continued to spew into me. I wrapped my other hand once more around his throbbing shaft and milked out shot after shot onto my waiting tongue. I held it in my mouth again as I knew that being new to the situation, he would love to see me swallow it. It was a big load again and I wondered when the last time was that he got off. His cock kept spasiming and shooting as his climax continued. It felt like he was dumping a whole can of mushroom soup into my mouth!

“Now it’s your turn” he said pushing me forward the wall with a twinkle in his eye. My own dick was a raging pole, something I couldn’t ignore as Justin’s fingers slid over my throbbing end. He got to his knees. He looked rather pleased with himself as he stretched his mouth and slowly slid it over the head of my cock. It was the tightest seal imaginable and made me wobble, moan and lean back against the wall in order to keep myself standing.

All I could focus on was the tight seal of his lips. His ruddy brown lips clasped around my dick; they were full and soft as was the rest of his mouth, especially his tongue which was used to great effect. It looked so good having him make a meal of my dick; especially, when he looked up at me.

Back and forth his head went. Up and down it bobbed. I moaned softly deep in my throat at his touch. When he grabbed my erect nipple and rolled it between his thumb and finger, I moaned louder.

I reached for him but he caught my hands and put them on my nipples and whispered, “Let me watch you play with them for a minute. I’ve never seen a man with nipples like yours,” obviously interested in watching me pleasure myself by fondling my nipples. Then after a couple of seconds watching me he said in a suddenly husky voice, “I’m going to suck you dry while I watch you play with them.”

His lips closed on my bell-end and he began to exert serious suction on my most sensitive body part. I would have fallen over, because my feet were trapped in my pants around my ankles, but even with his mouth full of my cock, he held me up, then glanced up to see if I was still fondling my nipples, and when he saw I was, he closed his eyes and concentrated on giving me the best blow job I’d can remember

At some point I lost my shirt, so I was standing there on the balcony of his penthouse completely nude while he preformed his magic on my most happy member, repeatedly bring me ever so close to the release of orgasm but never letting me quite get there.

The first time he stopped my orgasm, I almost fell over, gasping with the sensation, “Urrgghhhh, Uhhhhhh!” but he had anticipated it and held me up, saying, “Hang onto the rail, and enjoy the ride big boy. I’m going to make you mine.”

He teased me by repeatedly brining me close to orgasm, but when his hands slide up the back of my legs and spread my arse cheeks wide, I moaned as I felt the cool breeze on my warm sensitive arse hole,

“oh shit Justin, suck my dick man!” and I would have cum in his mouth, but he stopped me again, squeezing my knob hard as he said in a soft but commanding tone,

“Not yet. I’ll tell you when you get to cum.”

The longer he sucked me the more I became aware he enjoyed sucking me. I felt it in his touch, more than he could have verbally expressed.

When I felt him spread a cool lubricant around my hole, I pushed my bottom backwards trying to impale my eager slot on his fingers as he rimmed my slot, but he wouldn’t let me. He moved his fingers so they just barely made contact and tickled my rim as he held my cock tight in his mouth, all the while teasing me with his fingers lightly rimming my slot. I wanted to cum, I begged, “Finger fuck me! Please! Make me cum!” As I tried to get him to finger fuck me, but he just let me beg and continued to tickle my eager slot.

Finally, he noticed my legs start to give out and slid his thumb deep up my impatient slot, looked up at me and said, “OK, now you can cum big for me.” I gasped at the pleasure of feeling him penetrating me, and with excitement that he had finally given me permission to cum in his mouth. “Oh YES!”

He finally slumped back in the chair as his cock gradually started to deflate “Holy shit. I’ve never felt so fucking drained in my entire life,” he said with a grin of pleasure on his face.

“Oh shit, Dillon. Thank you!” he said enthusiastically. “Ummm, this will be our little secret, okay?” I nodded in agreement.

“Great! Uh……do you think we could do this again sometime?” he asked with a look of anticipation on his face.

“Sure, if you like.”

“Oh fuck! That would be fantastic. Look, if I’m going to be using your mouth on a regular basis, I’m going to give some of your work to Belinda so it doesn’t look like you’re falling behind. That should free up some good chunks of time for you to work closely with me. Okay then, you better get back to work now.”

What a day it had been!

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