Hotel Hookup

It was my first time traveling for business and I was looking forward to it. I flew into San Jose in the morning, went straight to our office and met with my boss. After grabbing lunch with him he told me to head to my hotel and get settled in for the week. I was really excited to check into my room. It felt like a milestone to travel alone, stay in a hotel, visit a new city, meet new people, eat at different places.

The room was probably fairly standard, but compared to my modest apartment it seemed really nice. I tested the bed and surfed the tv channels for a moment before beginning to unpack. I looked for an iron in the closet to press my dress shirts for the week, and after not finding one called down to the front desk on the room phone. The staff who answered my call told me to bring my clothes down for a complimentary service that I assume was part of our corporate deal. Impressed, I finished unpacking and gathered the shirts I wanted ironed. I took the elevator down to the lobby and waited at the front desk. There was a guest in front of me being helped so I waited patiently, taking in my surroundings.

As I examined the décor, shirts tucked under my arm, a man caught my eye passing through the lobby and turning down the opposite hall. I only saw him for a moment, but he looked like my type. He was wearing short swim trunks and obviously headed out for a relaxing afternoon. I shamelessly stared at his thick legs and ass as he walked away and let my imagination run.

"Can I help you, sir?" The hotel staff interrupted my daydreaming.

"Yes, I called about having some shirts pressed."

"Oh, yes. I will take those, sir." I handed him my shirts and he explained that they would give me a call when the shirts were done.

I thanked him and made a beeline to the pool area, hoping for a closer look at the man who caught my eye. Without thinking, I walked out to the pool and found him reclining in a chair, reading a book underneath the shade of a large umbrella. He was wearing short navy swim trunks and a cut off that exposed his bulky arms, a mass of muscle and fat that seemed to typify the rest of his body. He glanced up from the book and looked right in my direction. I swiftly diverted my eyes and tried to look inconspicuous, suddenly realizing I was helplessly out of place standing by the pool, alone, in my dress clothes.

"Looking for something?"

I looked back in his direction, praying he wasn't talking to me. There was one mother with two small children at the opposite end of the pool, but no one else. He was clearly talking to me. "Oh.... no, I was just... checking out the pool." I paused, further unnerved by his smirk, and then added, "I was thinking of taking a dip."

He nodded, still smirking: a look that assured me he didn't buy my alibi. Almost as if he were testing me, he set his book down and sat up in his chair. He grabbed the base of his shirt with both arms and lifted it over his head. I turned away.

He walked to the edge of the pool in front of him, ten feet to my left, and sat with his legs dipped in the water and continued leafing through his book. "Water's nice."

Unsure of how to act, I just smiled shyly and headed back to the lobby to go back up to my room. I wondered if he watched me go, as I had watched him moments before, but didn't dare turn around to check. As I stood alone in the elevator I contemplated my options. I almost felt obligated to change and return to the pool so that it wasn't glaringly obvious that my excuse was fabricated. If I headed back to the pool and took a swim maybe it would be more believable that I wasn't caught shamelessly staring. But, I was also apprehensive about being seen. There were going to be plenty of my co-workers staying at this hotel, many of whom I'd never met before.

I decided to go for a quick swim. I was just going to relax, enjoy the sun and the water, and come back to my room.

When I returned to the pool, the man was back on his chair in the shade. He was wearing sunglasses, hiding whether his eyes were open or closed, but I didn't dare look his way. I found my own lounge chair and laid out in the sun, closing my eyes and enjoying the warmth.

I wondered if he was staring at me the way I had gawked at him before he noticed. The heat felt nice for a while, but I quickly understood why he was in the shade. I needed to cool off so I sat up and headed for the water but when I got up, I noticed that the man had left. I was disheartened until I noticed he'd left his book behind. I turned to the lobby door to see if I could catch him but he was nowhere in sight.

I thought I'd better try and return his book. It was only polite. I headed towards his chair and picked up his book. As I grabbed it, I immediately noticed a small hotel sleeve - the plastic cover they give you with your room key when you check in. Room 304. I debated whether this was all intentional or not. It seemed plausible enough to conceive he could have accidentally left the book behind and used the sleeve as a bookmark. But it seemed calculated. He knew I'd look over and see his book and that I'd be eager to return it. The whole interaction seemed pretty forward, but I was bad at reading people and also guarded against embarrassing myself by assuming he was interested. I also wasn't sure I wanted anything more. I have fantasized about men like him for years, but I'd never actually been with another man. I skipped my swim and headed back inside the hotel.

I walked through the hall and into an empty elevator, contemplating my options. I was going to head back my room and take my time. Part of me begged to let go and see where it went. I felt this indescribable urge just to see him again, but my mind battled the feeling, reminding me of all the reasons I shouldn't indulge my thoughts.

I could leave a note with the book explaining what happened or even give it to the front desk and have them return it to him. Or I could just politely return it to his door. Nothing is going to happen anyway. You're overthinking it. The back and forth waged on in my mind when the elevator dinged and I stepped off, only now aware I had inadvertently pushed the button for the third floor instead of my own. As I stepped into the hallway I panicked and almost turned back to the elevator, but I could see Room 304 just down the hallway and something stopped me.

As if everything else around me had disappeared, I slowly and hypnotically approached the "3-0-4" unable to see anything else. I unconsciously knocked on the door and, all at once, realized what I was doing. I froze with fear, and the door opened. He stood before me in his plush, white robe.

"I..." It was my first good look at him, and I became flustered. He was stunningly handsome with intense eyes, chubby cheeks and an imposing presence. "I believe you left this at the pool." I offered him his book and he grabbed it with a smile.

"Thank you, son. Why don't you come in?"

I panicked and stammered, unable to give a response. I was overwhelmed with lust. I couldn't even bring myself to meet his eyeline, staring instead at his chest. His robe was tied shut but revealed his white hair and soft, lightly golden skin. I finally looked into his eyes for the first time and knew I was caught. "I.. can't" I finally muttered. My eyes never left his.

He took a step closer and I froze. My body trembled in a way I'd never felt. I knew it was my last chance to get away, but I couldn't seem to move at all.

"I can't." The words were empty.

"We both know why you're here." He grabbed my erection through my shorts and my surrender was complete. I feebly fell into his chest, intoxicated by his proximity.

He pulled me inside and shut the door. My dick throbbed in his hand, aching like the rest of my body for more. He sat me on the edge of his bed and knelt in front of me, grabbing the waistband of my swimsuit and pulling them off. My erection sprang to life and was quickly engulfed. The feeling was overwhelming. I was no virgin, but I had tried my whole life to suppress my homosexuality. My prior experiences were purely physical and immeasurably less satisfying than this. I accepted I was gay years ago, but this was my first real sex. The incredible physical feeling was matched with an insatiable desire.

My whole body tingled as he swallowed my dick. I squirmed and shifted, arching my neck back towards his headboard. I wasn't going to last long, and I was desperate to feel his body.

I sat up straight, gently lifted his head off of me and brought him to a standing position in front of me. I slowly pulled one end of his belt, undoing the knot and causing his robe to fall open. His own erection stood right at my eye level, poking out from an all-natural bush of gray hair. That hair extended all over his legs, round belly and chest. I slid my arms around his waist grabbing his cheeks and pulling him towards me, eagerly taking him in. I had craved this my whole life and impatiently sucked on his cock. His hand naturally rested on the back of my head and assisted as I energetically bounced and bobbed around his cock. Without slowing, I looked up and watched as he enjoyed my eager mouth.

At first, his head was craned back like mine had been. He grunted periodically and when he did his hand would grasp my hair a little tighter, encouraging me. His body was so strikingly manly. He was strong but soft, overweight and naturally hairy. My hands travelled from his ass to his thighs, gently raking through his hair and massaging his legs. He looked down in my eyes and began to use a little more force.

"I can spot a cocksucker when I see one, boy." I flinched at the word before realizing its accuracy. "Most people don't pay old men like me any mind."

He pushed me deeper down his cock and held me there, pushing his pubes into my face and interrupting my flow. I was losing my breath, but wanted him to use me. He released me and moved me back and forth again, re-establishing my rhythm.

"So it's easier to notice when some do."

I bobbed up and down on his remarkably thick shaft.

"Some boys just can't resist a real man when they see one."

I moaned on his dick and he accelerated our tempo with his hand, which now completely dictated my movement.

"You were desperate for my cock, weren't you boy?"

I moaned my affirmation and focused on my task of pleasing him.

"So why pretend, boy?"

He pushed me down all the way again, tickling my throat with his hair and blocking my air.

"Don't lie to Daddy."

He released and bobbed my head up and down again.

"You followed Daddy out to the pool like a lost boy and then pretended to be looking for someone else."

He stopped me on the tip of his cock and tilted my head back to look in his eyes.

"Couldn't fool me, boy. I knew you were a cocksucker. Lie to me again. Tell me you don't want it."

"I need it, Daddy."

"Need what, boy?"

"I need your cock."

He pushed me back down and continued to use my mouth as he pleased. I was close to cumming already from all the stimulation. He was getting closer himself as his breathing became unsteady and he occasionally moaned and grunted. I was eager to taste his cum and started flicking the tip of his cock with my tongue as he moved me up and down. He sustained a deep, manly moan as he got closer and closer. I started to become desperate for his cum. I needed to taste him, but more importantly I needed the satisfaction of giving him pleasure. His legs started to quiver and he promptly pulled me off. I was out of breath, and desperate to get back on him but subject to his will.

"You ever bottomed, boy?"

I shook my head no.

"Are you scared?"

I shook my head again, but this time I didn't mean it. I was nervous, but I didn't want that to deter him.

"Don't lie to me boy."

"Please take me. Fill my hole with your thick cock." I grabbed his wet cock and slid my hand along his shaft. Daddy shook off his robe, revealing his entire perfect body and I noticed sweat had started to bead on his skin. I stared at the white chest hair scattered across his round pecs and enticing nipples. My eyes continued downward to his round belly with darker, grayer hairs circling his navel. I leaned forward and kissed his belly, letting go of his prized cock to grab his sides. I lifted my head and rubbed his belly with both hands, savoring the feeling of his skin, his hair, his warmth. "Please, Daddy. I need to feel your body on top of mine. I need your belly to fill the crevice in my back as you take what's yours. Use me like a real man."

My hand found his balls and playfully rubbed, trying to stimulate him further. I looked in his eyes and waited for his next move. He pulled me up and turned me around, wrapping his arms around me and pulling me into his massive frame. His stiff dick pressed against my skin, I felt his heat and closed my eyes. He whispered directly into my ear, with a low growl. "I'm going to make you scream, boy."

My cock twitched and my head rocked to the side, granting him easier access to my ear.

"You better be sure because once I start, there's no stopping what I'm gonna do to you."

He started grinding his cock against my skin and I conformed to his touch in response, hypnotically moving my hips along with him.

"Fuck me," I softly pleaded.

He moved us forward and carefully fell onto the bed, pinning me down beneath his body. His weight drove me deep into the mattress, reminding me of his physical dominance over me. He lifted up momentarily and I felt a gel squirted on my lower back. Daddy rubbed his cock in the gel, sliding across my skin while coating himself with lube. His balls pressed into me as he began thrusting across my back as if to give me a preview of what was to come. My own rigid dick was pressed into the bed and threatening to unload right into Daddy's sheets.

Apparently satisfied with his preparation, he positioned himself behind me and I nervously anticipated what I'd dreamed of for years. Daddy's lubed dick was slippery enough to penetrate past my first barrier easily but my body resisted him pushing further. He persisted and pushed deeper and deeper as my body tightened and squirmed against the unfamiliar feeling. I cried out beneath him, burying my face in the mattress to stifle the sound as a pressure built inside. A pain seared through my ass as he slowly plunged all the way in, his balls resting against my skin. I was panting into the sheets and quickly starting to sweat. He leaned forward onto me exactly as I'd begged, his belly pressing into my lower back and his chest nestled against my traps. He wrapped his arms underneath my torso and made short, slow thrusting movements.

My body was doing everything to fight - squirming to try and escape the pain, panting and gasping from the mounting pressure. His weight bore down on me, restricting my diaphragm and his arms squeezing my ribs. His thrusts only added pain and I moaned and moaned loudly into the bed, hoping he'd never stop.

"Relax, my boy." He growled in my ear.

My body was tense from all the strain and pressure. I focused on elongating my breathing and trying to ease the tension.

"Don't resist Daddy's cock."

He added a bit more to his thrusts, but was still careful with me. I could feel his labored breaths on my neck and hoped that meant he was enjoying himself.

"Embrace it. Take that fat cock."

I moaned into the sheets. It felt like my whole backside was on fire as the pain of him stretching my virgin hole fused with the heat of being smothered by his massive frame.

"You wanted it," he grunted and really began to ram me. "There's no escaping now, boy."

He reached a pace brisk enough for his balls to gain momentum with each thrust, slapping against me as he pounded my hole. Our bodies became slick from exertion and his belly slid around my lower back, his damp hair and skin sweetly rubbing against my smooth crevices.

It was everything I wanted, but the pain was real. My body contorted in response to his increased vigor, which caused my head to lift upwards and unmuffled my cries. I yelled unrestrained as Daddy relentlessly worked, just as he'd promised.

He gripped the back of my hair, using his other hand to lift his torso off my back without missing a beat. He planted his right hand firmly above my tailbone, where his belly was before, pushing me into the mattress and creating an awkward arch in my back as he lightly tugged my hair. I grimaced and grunted with each rapid thrust.

"Beg for relief."

I yelled loudly, as a powerful thrust sent a sharp pinch through my nerves.

"Beg for a break. A chance to suck Daddy's cock again."

"No...." I begged, but not for a reprieve. With a pathetic strain in my voice I groaned. "Don't stop."

"Oooo," Daddy seemed pleased by my determination. "Did you say harder boy?"

The stimulation heightened as a sensation formed in my core and seemed to pulse outward through my body. I gasped as the feeling took over my thoughts.

"I'm gonna cum. I'm gonna cum, Daddy."

He rose quickly, effortlessly flipping me around on my back and pulling me to the edge of the bed. He pushed right back inside me and I looked up at him through the stars flooding my vision. He pounded my hole and pumped my simmering dick.

I moaned continuously as I erupted, spewing clear, liquid boy-cum all over my chest. My body convulsed uncontrollably as he milked my dick with his meaty hands, torturing my sensitive glands with his thumb.

"Look at that nice little boy milk."

I was still orgasming, in a daze as Daddy steamrolled my hole and played with my flimsy cock. He let it drop and I felt the last of my cum leak onto my thigh.

"You ever seen a real man's load, boy?"

That snapped me out of my daze. I whimpered as the diminishing orgasm allowed for the dull ache of his hammering to become the dominant feeling in my body once more.

"You want to see?"

"Oh," I moaned. "Please, Daddy."

"You want Daddy's load in your hole?"

I moaned and bit my lip, still actively fighting against the pain.

"Or on your face?"

I watched a droplet of sweat fall from his brow and splash against my cum-covered stomach.

"Maybe on your chest, next to your boy milk." He panted and another bead of sweat gathered on his brow. "So you can see it, and appreciate what a real man's seed looks like. Huh, boy?"

"Please Daddy. Anywhere. Give me your seed. Make me your boy."

His moaning became more urgent and his legs bucked as he pumped in and out of me. It thrilled me to hear him reach orgasm. He pulled out and convulsed, my hole grateful to be relieved, as I watched as Daddy's meaty hand pointed his slit at me and thick, white cream shot onto my exhausted body. It was his turn to fill the room with cries as his body shook and his cock spasmed. He jerked his load out as jet after jet of cream sprung across my smooth skin. I relished the sight of his belly shaking and his mouth contorting as he finished unloading on me. His cum was so much thicker and creamier than my clearer, liquid semen. It was a sticky, viscous texture with more color and substance. I watched his thick fingers coax the last of it out.

A slightly yellow, white goo clung to his cock like toasted marshmallow. He let go of his spent cock and caught his breath, and I was transfixed on the irresistible sight before me. I sat up and leaned forward, feeling my boy milk dribble down my abs as I licked the cream off his cock. The sweet but musky cream was delightful, and I craved more. I engulfed his softening cock, licking the last of his flavor from his shaft. Sensitive to touch, he bucked in my mouth. Daddy grabbed my head and pulled me off, but then used his thumb and traced the length of his cock to coax out the very last drop of his cum. I positioned beneath him with my mouth wide and tongue extended as it dripped down like honey.