Should I Keep Him? Erotic Story

Should I Keep Him? – An Erotic Story

Now, I could sit here and bore you with every other little detail. How I got where I’m at in my 45 years of life. How I’m a rather tall guy with handsome features. I could also tell you about all my failed relationships but all of this would take forever.

I could also tell you about how I built my company from the ground up and that lack of confidence is something I know nothing about. No, we’ll skip all that.

There is only one event I need to discuss with you, my assistant Sam, his first business trip. So, gather around everyone, let’s get to it…

Should I Keep Him? Erotic Story

The first couple of days of the trip were uneventful. The days went as planned and there were never any surprises. My team of lawyers, accountants and partners kicked ass. They were fantastic all week, on point, ahead of the curve as it were. Sam was on point as well. It was as if he knew what I was going to ask for before I asked, well done Sam. I got everything that I wanted and more before finally closing the deal.

I immediately informed my team that this merger meant they could expect to be well compensated and since it was already late in the afternoon, they could stay the night and go out, enjoy L.A. on me.

I turned and looked at Sam, “Hey I know I can be an asshole but you did great. Go have some fun and stop being such a tight ass. You make me nervous.”

“I’m good sir and if it’s just the same to you I think I’ll stay in so that everything is ready for check out tomorrow.”

With that he smiled and went on his way. I couldn’t help to think that there was something wrong with him.

I eventually returned to the suite, walking in just as Sam was getting ready to go into his room, I couldn’t help but admire how nice he looked. Sam is a small, well-kept 25 yr. old young man. I’m guessing 5’5”, maybe and a very tight body so I know he works out, he has to. Sandy brown hair and blue eyes, not that I’ve noticed or anything.

“Everything ok sir?” His question bringing me back to the now.

“Yes Sam, everything is just fine.”

Yeah, I was admiring him but I wasn’t about to let him know that he caught me off guard. Then without another word and just like that he was in his room, door closed, gone.

“Strange little guy,” I thought to myself.

I was exhausted and after a good nap I went for a run and swim then a quick shower afterwards. Thinking that I was alone I headed out into the living area of the suite with only a towel around my waist and one over my head as I dried my hair off. I stood there contemplating my evening when much to my surprise Sam steps out of his room.

“I thought you were out?” I said with a quick glance.

“No sir, I decided to stay in and like I said, make sure that everything is ready for us when we leave in the morning.”

It’s always the little things that impress me and his attention to detail is why I thought that he wouldn’t be my assistant much longer. Like my other past assistants, I’d probably have to promote him too.

He was wearing a white t shirt and white pajama pants that accented a very nice pair of legs and even nicer bottom. Sam had curves and very soft features complimented by a nice tight body.

Once again, I must have lost track of myself. I was looking into his eyes for just a moment too long. Instantly he broke eye contact and looked down at the floor as he fidgeted with some papers that he was holding onto. I stood there, pretending not to notice throwing the towel over my head, drying my hair. I knew that he was still in the room. I could hear him fidgeting.

“I was going to go out myself but I changed my mind. How bout I hang out with you instead.”

Allowing the towel to hang over my neck as I finished my sentence, I gazed up, he was looking at me.

Just as he was starting to blush, his eyes lowered, pausing to gaze at the towel around my waist. I didn’t realize it but I was starting to get hard. I didn’t have to look because his facial expression and the sensation from my cock said it all. I’m a rather above average man when it comes to my cock and I’m sure that the towel around my waist wasn’t holding it back.

I knew that gaze, that look and even though it had been over twenty years since I allowed myself to enjoy a man, I wanted this one.

“Come here.” I called out.

“Sir?’ His response, in a soft voice.

“It’s ok, come here…” I repeated.

I watched him as he took the steps necessary to stand in front of me. I reached out, taking his face in my hands I could hear a gentle gasp escape his mouth as I pulled him close until he was on the front of his feet, I lowered my face to his. I kissed him. A soft gentle kiss barely allowing myself to put any pressure on those soft full lips.

It was right then that I noticed, Sam has wonderful kissing lips, big and full. I continued kissing him, gently pushing his lips apart with mine. Until, finally, he was returning my kiss with his open mouth, I made sure not slip my tongue in his mouth. If he wanted my tongue, he would have to come for it.

I didn’t have to wait long. Sam slipped his tongue in my mouth and slid his hands around my back pulling himself up to me as I pushed his tongue back into his mouth and allowed myself to tongue fuck him. Now he was on the tips of his toes, his head tilted back and the sounds of our lips smacking while we kissed and kissed.

Without breaking the kiss, reaching down, I picked him up in my arms. Cradling him, carrying him into his room. Carefully turning the door handle as I held him, kissing him. As the handle turned, I kicked open the door and made my way to his bed. Putting him down by the side of the bed, positioning him in front of me as I removed my towel before sitting on the edge.

I moved my feet, my knees apart and allowed him to move between my them, he quickly began kissing me again. Reaching down I grabbed his shirt, breaking our kiss so that I could pull it off of him I was pleasantly surprised.

Sam was smooth, nicely tanned with a firm toned body. Oh, and those nipples, they caught my attention.

Beautiful nipples on top of large light brown, areolas. With his level of excitement at that moment, his areolas were swollen. “Sam has puffies.” I thought to myself, I instantly took one then the other in my mouth. I was suckling his nipples as he tilted his head back, pushing his nipples into my mouth. He began moaning and whimpering and my cock? Rock hard.

Pushing his body forward he could feel my cock pressing against him and that was all he needed. Sam began lowering himself, taking those wonderful puffies away from me. He was kissing my face, my neck, my throat and finally making his way to my chest.

I’ve always made sure to take care of myself, stay in shape, Karate, that sort of thing. Not because I want to look good or be a bad ass. I do it because I’m afraid of death. The big hairy, chiseled, muscular chest is just a wonderful result of my fear.

I allowed him to suckle my nipples, briefly, allowing anyone to fondle my nipples is not my thing. I gently pushed him away from my nipples, he seemed to pout, he looked precious. However, that cute little pout was instantly replaced by a soft gasp as his eyes caught sight of my now fully erect cock. 

Just like that, he was on his knees and with his mouth on my cock. I leaned back catching myself and tilting my head back as he worked my cock with his tongue and his lips. I was impressed, Sam was really good at this because he didn’t try to take it into his mouth right away.

He went slow, sliding his tongue all over the head of my cock and flicking the tip of his tongue across my pee hole. Playing with it like I play with a woman’s clit when I start to go down on some really nice pussy. Then he began suckling my cock as if it was a big lollipop.

I watched as he started the process of opening his mouth to allow the head of my cock in. The sight of his mouth stretching, the head of my cock pushing its way into his slobbering, wet mouth, it was obscene.

With one hand on the shaft and my cock in his mouth he began…

Try as hard as he may, he could only fit half of my cock into his mouth. He wasn’t going fast, he was being deliberate, slow. Taking care to properly suck my cock. I allowed him to suck my cock for a moment but I needed more. Since the day I hired him I had often wondered just how good his nice heart shaped ass looked without any clothes blocking the view.

I’d stolen many glances at his ass and knowing that I was finally going to not only see it but have it caused the anticipation level inside of me to almost burst or at the very least blow a load in his mouth. It was to soon to cum, not yet, I told myself.

“Stand up.” I called out. My deep voice startling him. “I said stand up!”

Quickly he jumped to his feet, “Yes sir,”

“Turn around and take off those bottoms.”

The look in his eyes as he coyly bit the corner of his bottom lip. The slight hesitation before slowly turning his back to me, beautiful…I thought to myself.

As he slid his thumbs inside the waist band I called out, “Slow!”

I could tell that my voice was making him nervous by the sound of his breathing. But what happened next caused me to take a deep breath myself. Hooking his thumbs inside the waistband of those bottoms he slowly started pushing them down.

Slowly his tan lines began to reveal themselves to me. Tan lines which allowed me to fully imagine what he wears while laying there tanning that fine, sweet ass. As he kept pushing down and his ass started coming into view, I could see the familiar triangle outline of bikini cut bottoms.

The tan lines highlighting the fullness of his heart shaped ass. The line across his back barely over his hips. The thin line moving around his hips over his legs, making his legs appear longer than they actually are. Finally, the triangle frame over his ass revealing his naturally creamy white skin, letting your mind envision those ass cheeks just barely spilling out of those bikini panties. Bikini briefs? Who cares, “I’m fucking him, oh yes. I. Am. Fucking him!” I thought to myself. 

When his bottoms finally made it to the floor, I was able to finally take in that wonderfully gorgeous smooth body.

I’m not into a man’s cock but with that creamy white area in contrast with that wonderful tan, I couldn’t help but appreciate his modest little cock resting on top of those impressive oversized balls. They were huge, full and pink. A smile escaped the corner of my mouth. 

It was all that I needed. I stood up and threw him on the bed, his breath escaping him as he landed on his back…

“Pull your legs back.”

I was commanding, I knew I was about to lose it, there was no request in my tone.


The loud stinging sound of my hand coming down on the side of his thigh, the simultaneously loud gasp escaping from deep inside his throat, the instant imprint of my large hand on his thigh. I was gone, my lust was in control now and not everyone can take what I offer once I reach this point.

Weather he could or couldn’t take it, it made no difference to me at this point. I was going to do what I wanted.

Grabbing him by his ankle and turning him slightly on his side so he could offer me that precious ass cheek… SMACK! SMACK!

I couldn’t help myself, the loud stinging sound of my hand coming down on his ass, the loud squeals escaping his throat and the deep red handprints on his untanned creamy white ass was making me high.


“Ohh…please sir.”

Sam, whimpering, the blush on his face only serving to trigger me again.

“What? What is it baby, do you want me to stop?”

I softly growled as I gently ran my hand over his firm bruising ass, soothing him.

“It hurts, I’m scared…”

As he said those words, he continued to gently whimper, I stopped.


After two more… I stopped.

Crawling up on the bed, grabbing him by his ankles I pushed his legs further apart, further back. I looked down as he lay there writhing like an innocent babe, hurting, pouting, knowing that he was about to be fucked, his eyes wide, as he reached up wiping his tears from his face with the back of his hand.

In the short time that he lay there with me hovering over him, I could see slimy smear marks on his lower abdomen just above his crotch, his tiny semi hard cock was drooling precum uncontrollably. I knew I could continue with what I was doing, spanking him, but something caught my eye and lust had other ideas.

I saw a glimpse, there it was, the jewel. I pushed his legs back, bending them at the knee stopping when his knees were pressing against the mattress. I wanted that, that precious hole. The pink color highlighting it against the backdrop of his creamy white skin in the crack of that luscious ass. The shape almost oval, a slight ring, like a small, puffy, tiny pussy. The hole dilatated enough, that if I wanted, I could slip the tip of my pinky finger in with little resistance.

I put my middle finger in his mouth so that he could lube it with his saliva. Reaching down I pushed my finger deep inside of him causing him to take a deep breath then slowly exhale. Without any delay I began finger fucking him as I probed for his prostate. Finally finding it, now I could really increase the flow of his precum. 

I began milking him then taking his slimy drool from his cock and smearing it on his hole. He was moaning with each tug of his tiny cock and each push against his prostate. The sensation of my slimy fingers smearing that tiny hole of his was making him start to writhe with lust.

I was milking him and using his own fluids to lube him, preparing him for what was next.

“If your dick gets hard, I will stop. Do you understand me?” 

My comment seemed to briefly catch him off guard. I watched him, he took a deep breath and I could see him, calming himself.

“Yes sir,” he replied softly.

Finally, he was lubed enough and I finger fucked him for a few more minutes until I knew he was ready. Placing the large head of my swollen oversized cock head on his opening I pushed.

Instantly Sam latched onto my forearms with a tight grip.

“Relax babe, just relax.”

The sound of my voice seemed to soothe him, to calm him. Again, I pushed and this time his tiny hole opened for me. I broke his seal.

I pushed deeper; I could tell that I wasn’t his first but I could also tell that it had been awhile since he’d been properly fucked. I fucked him slow at first until his facial expressions and his breathing told me that I was hitting his spot just right. Within the first few strokes he was blowing his first load of cum all over his stomach and his chest.

“Oh god, oh god, I’ve…I’ve nev…never done that.”

His eyes were wide as he spoke in awe. His breathing was racing and his thighs trembling. I didn’t allow him to totally take his first prostate orgasm in, to enjoy it, to appreciate it. I reached down and scooped up as much of his cum as I could.

Pulling out of him I proceeded to smear his cum all over my cock and again over his hole. Looking at that innocent face with all it’s beautiful features as he lay there gasping trying to absorb it all I knew what I was going to do and I really hoped that he could take it.

Throwing his legs over my shoulders, with no hesitation I shoved my cock deep inside his tight little ass. He screamed and I began the torturous session of bottoming out his tiny hole with my thick long cock. Over and over, listening to my balls slap against the bottom of his ass cheeks. Sam was lost, his head flailing side to side as he cried out with each thrust.

I slowed myself long enough to look down, watching as his asshole clamped tight around my cock, developing a suction grip. I slowly slid my cock out, the sight of my thick shaft glistening, the suction grip of his hole causing his insides to appear as if they were being pulled out. His insides clinging to my cock then disappearing as I shoved back inside of him, deep.

At times would I pull my cock out so that I could marvel at how wide he had dilated, his asshole stretched, fully gaped. Then I’d slam my cock back in deep. The trapped air escaping every time I’d pull out. Queefs escaping his hole causing him to moan loud after each one. The night had turned into one big filthy, perverted, mess.

I put him on his back, on his side, I bent him over like some common bitch in heat. Fucking him for hours, fucking him to tears, to screams, to moans, to every sound a person can make while being mercilessly fucked. Pausing only after his orgasms to collect his cum, to continuously lube my cock with his own cum. So, I could keep fucking him.

I lost count of the number of times he blew his cum over us. In the end there was no cum only his quivering body beneath me letting me know that he was still trying to orgasm signaling to me that it was time to finish. I filled him with all my seed as I let out a loud yell of my own. I couldn’t remember a fuck as sweet as Sam and his tight little ass was amazing.

It was a wonderful night, I had fucked him all night and well into the morning before finally falling asleep with him in my arms, spooning him, my cock eventually going limp in his ass while we both slept.

I might not be promoting Sam anytime soon… let’s see where this takes me. I might keep him.