Why Him, of All People

Why Him, of All People?!: 
Chapter 1 - You can call me boy

“Hi, daddy.”

“Hi… please don’t call me daddy.” I was nervous as it was. He was eyeing me shamelessly, and I felt extremely uncomfortable.

Nevertheless, I let him pull me in. Checking anxiously if anyone was out there seeing us.

“And how would you like me to call you?”

“I am Sam. What is your name?”

“Are we introducing ourselves, or is that a fake name?”

“Should I have made up some?”

“No, but it’s clear from how tense you are that this is not something you usually do, so I thought you would like to keep it as hush-hush as possible,” he pursed his lips mockingly and crossed his arms.

“Right… well, I am really called Sam. But otherwise, you are right.”

“Cool. I prefer it that way myself,” he smiled. 

“Still, I would like to know your name.”

“You can call me boy.”

“Boy?”

“Yeah.”

“How old are you?”

“25.” 
He nonchalantly walked into his bedroom and looked at me.

“Heck…” now I felt even worse. I was 37 last year. It’s not like I could be his father, but still, he was much younger than I had hoped.

This was a terrible idea. I thought if I should leave. I created that account on a whim because I was horny, and honestly, I was jerking off at that moment, so I cannot say I was thinking clearly. When I saw his message, I was instantly at the edge, and after a couple of not-really informative replies, I just jumped in my car with still raging cock and came here.

“Have you at least been with a guy before?”

I shook my head in negative. I was looking at him, worried.

“Are you even into guys?” He sounded suspicious now.

“Yes, but I was married for the last thirteen years, so I didn’t do much about it.”

“How come?” he sat on the bed and spread his legs.

I looked at him under that bright light. He had blond, longish wavy hair up to his shoulders, and the tight shirt that was like painted on him showed his ripped torso. He was maybe 180 lbs and was taller than me. He could be 6’1 or 6’2. He had green eyes, a clean shave, cute boyish look, yet there was something very masculine and manly about him despite his age and appearance. Something in the way he presented himself. He was perfect! Damn, better yet, he would be perfect ten years ago when I wouldn’t feel like I was about to molest a minor.

“Accident. She became pregnant, and we thought we loved each other, so we decided to get married.”

“Right. You divorced?”

“Yeah, she got custody, of course.” I was still hurt about that, but with the bar, I am running; maybe it’s for the best.

“Right…” He looked like he was getting bored.

“How does this usually work?”

“Usually, I wouldn’t be talking from across two rooms. I would probably be naked by now and either suck your cock or, if you were very demanding, your cock would be deep in my ass.”

I looked at him, flustered.

“Right.” I still couldn’t move. This was getting awkward.

He rolled his eyes and came to me, taking me by the hand and leading me into the small living room. Then he sat me down on the square couch and stood before me.

“Do you like what you see?”

“Yes.”

“Are you hard now?”

“A little.”

“That’s a good start, Sam. Tell me what you want?”

“I don’t know.”

“Can’t do that,” he winked at me.

I chuckled a little bit and forced my eyes to meet his.

“Tell me,” he whispered softly.

“Take off your shirt?”

“Is that a question?”

I frowned, not really catching up.

“Say it like you mean it, Sam.”

I took a deep breath. I am here already, anyway.

“Take off that shirt.”

“Damn! I like that tone, Sam.”

He raised his shirt and pulled it over his head.

“Damn!” I couldn’t help saying that aloud. He was amazing! His small nipples proudly rested in the middle of his pronounced pecs, with light hair towering above a ripped six-pack and a trail of hair covering his belly button that got thicker as it reached under his pants. I couldn’t stop looking at that spot that hid the rest.

“Pants.”

I watched him untie them and slowly move them down. Then, after agonizing seconds, I saw he was not wearing anything underneath! Instead, there was a thick trimmed bush of light brown hair on top of his hanging cock.

I took a sharp breath.

He turned around, and I feasted my eyes on two perfectly round globes in front of me. They were covered with light fur and thickened above his crack. I saw as in a trance like they spread a little when he bent all the way, pulling his pants down his muscled legs.

I felt my dick harden and unconsciously rubbed it in my jeans.

He turned to me and watched me with a smile.

“When you thought about fucking with a guy, did you want to be the one fucked or the one doing it?”

He could have asked whether I see myself as top or bottom. One can pick up a lot even when they are not leading an active gay lifestyle.

“I would preferably top.”

“Good. When we texted, you said you were jerking that cock. Show me.”

“You want me to masturbate in front of you?”

He chuckled and knelt before me.

“Please,” he said it so sweetly that I couldn’t stop myself from caressing his face and combing his hair back.

I opened my jeans and took out my hard dick.

“Damn! It looks even better than in that pic!”

I stroke it while looking at him.

“Tell me, Sam, what turns you on?”

“I don’t know if I have some sort of a kink. I never really had the chance to explore that.” I suppose I liked when Madison dressed up for me, but I wasn’t sure how I would like that with a man.

“Very well. Then sit back and let me try something.”

He went away, and I just sat there. When he returned, he was wearing black lace panties with silk ribbons.

“I usually bring these to the second date, but seeing you will not take much initiative, I am going with what I like.”

“Fuck!” My dick jerked so hard that a blob of precum ran down one side. He saw that, and I could see his eyes fixed on it with a broad smile forming on his full lips.

“You seem to like it.”

“Do you have stockings?”

He smiled and went again to his bedroom.

When he emerged, I stood up without thinking. I came to him and pressed him against the wall running my hands over the soft material.

“They feel nice.”

“You feel nice.” 

I looked at him. He stared at my lips and back into my eyes; it felt like he was going to kiss me. I looked down at those legs in black nylon.

I always loved those on Madison. It was one of those things that got me worked up. I knew I would much rather see a bouncing cock under me than her tight pussy, but these just did it for me. Seeing them on those round cheeks, ripped legs, and tenting cock underneath was making me crazy. I suppose I never thought I would see it on a man. So I do have a kink, probably.

He turned and put his hands on the wall. I pressed my chest on his back and humped his covered butt. I breathed harshly. I hoped I could rip it on him and fill him with my load!

He pushed his ass to me and arched his back.

“Lick it!”

I sank to my knees and started running my tongue over his crack. He moaned slightly.

“I want to rip them and breed that hole,” I growled.

“Fuck!” He jerked under me as he heard that.

I spread his legs and rubbed his cock, tenting those panties and stockings.

“Rip it!”

With a single pull, I tore them on him, sliding those panties to the side and diving into that pink asshole. I loved that he had hair there. It just reminded me more of the fact that he is a man. He screamed and pushed against me.

One thing I am proud of is that I am good at eating pussy. Give me an asshole, and I am in fucking heaven! I didn’t even start slowly. I rammed my tongue into that sweet tissue and made it twitch under me. He was loud! He moaned so sweetly that the sound of his baritone growls just made my cock leak more! I couldn’t get enough! I rubbed his legs, enjoying the feel of nylon, and then cupped his contained balls. I wanted to taste them!

I stood up, and there was now no timidity in me anymore. With crazed eyes, I looked at him, pulled him into my arms, and pushed him onto the couch. I watched him fall and spread his legs for me so seductively that I couldn’t even think straight anymore. I tugged on the front, and the sound of tearing fabric made me moan.

I stared at his hard shaft under the lace and traced it with my hand. I looked into his eyes, and his parted lips instantly drew me in.

I stopped myself mid-way. Something in me kicked, and I couldn’t move.

He took one of my hands and started licking my fingers and moaning. Then he spread his legs wider and put my hand on his ass.

I got the hint and pushed in one finger first, then after a while, added a second. I started slowly, but after watching his blurry eyes and lips part in lust, I began to finger his hole fast. He moaned and breathed roughly.

“More!”

I added one more finger, and he put his big toe to my mouth. Fuck! I started licking it and sucking, watching him stroke his cock and look at me.

I held his ankle and feasted on that foot, feeling my cock cry for attention!

“I want to fuck you!”

“Fuck! Please! I am getting crazy here!”

I pushed him to move a little and joined him on the couch, aiming my cock at his asshole. I made every effort not to ram into him my whole dick. I am a little under nine inches, and my grit is wide. I knew very well how hard that could be taken. Especially the first time. I pushed in the tip and grabbed his sole, licking the arch of his foot. 

Then, with desperate movements in and out, I slowly pushed in half of my cock, watching him hiss and breathe deeply under me. I was shaking by the time I was in up to the hilt. I felt him squeeze me in rapid intervals, and it was maddening, but I could tell he was trying to get used to it. I waited and spent my time bringing one then other his foot to my mouth and worshiping them.

“You are just fucking perfect, Sam!” he breathed out.

He smiled at me and squeezed me with his hole, this time, it felt more like encouragement.
.

“Are you ok?”

“Man! I am in heaven! Please fuck me!”

I didn’t need anything else. So I started pounding him slowly but increasing the tempo gradually until he was screaming and shaking under me, begging me to fuck him as hard as I could!

He was an incoherent mess when I saw him reach for his dick and stroke it. I knew by now the perfect angle for hitting his prostate, and knowing he was getting close; I made sure to aim at it with each trust. I bit his thumb and sucked on it until I heard his throaty roar and could see his load shoot out of his slit. His hole squeezing me for dear life, and that sight sent me over the edge, and with a loud moan, I shot into his ass so much cum that some of it leaked out of him.

I fell on the carpet under his couch and breathed heavily.

We fucked four times that night, and when we utterly spent fell on the bed, he chuckled that the sun was rising. I looked and agreed, realizing that he had fallen asleep. I somehow found the strength to go to his shower and leave.

I spent the rest of the day sleeping and woke up at my alarm at 7 pm.

In a perfect mood, I got ready and left for work.

“Hi, Sam!”

“Hi, Chloe. How are you?”

“Good, but you seem to be in a great mood today!”

“I had an amazing day.”

“Glad to hear that. By the way, is the new bartender coming today?”

“Right! Yes, he should be. I can’t wait to meet him. Gina was super excited after the interview.”

“Yeah! You are going to love him! He will make few ladies spend a fortune here.”

“Good to hear that. Let’s hope he also knows that we are not that kind of establishment,” I winked at her, and she grinned.

Gina came over. She is managing everything I don’t feel like doing and is the best one can hope for. I trust her judgment the most.

“Hi, Sam.”

“Hi, heard the new one is coming today.”

“Yeah, he is here already, just getting changed.”

“Great.”

We talked about the shift, and Gina also pointed out how good I looked. I have to say I felt terrific! Well, I did, until I saw a very familiar figure emerge from the back of the bar in a bartender’s uniform.

No way!

Why him, of all people?!

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I. Dusk