My first time cruising

The story of my first time cruising, I used the internet to meet a DADDY while holidaying in New York, and I’ve thought about him ever since

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  • 7 Min Read

What you are about to read is a true story, and it is one that I’ve been reliving in my head for the past 6 years.

It was 2019, and a younger version of myself was on holiday in New York with his parents and sister. I had grown bored and upset at spending time with them, particularly her, so I decided that I was going to pretend to be ill, as was a common habit at the time for me.

Another common habit of mine at the time was sexting gay men online, and getting off to our conversations, and so I decided that that was going to be my plan of action when my family left me alone in the hotel room to go shopping, or sightseeing.

The moment that my mother closed the door behind her, my phone came into my hand and I began searching for whatever site I could find. So long has since passed that I couldn’t even begin to tell you what website I decided upon, but I remember that it had a map function, a very important detail.

After about ten minutes of not being able to find any intelligent man to chat with, HE came online, listed as being within 150 feet, he immediately reached out to me. Funnily enough, I remember his opening line like I received it this morning. “Hey, I’m Aaron, 43, what’s up?”

43 YEARS OLD! He was older than my father, that detail made my cock twinge with pleasure, I replied back coyly, telling him that I was 18 and giving him my name, hoping to get under his skin, receive a picture or text that would allow me to jerk off to completion before closing the window and watching TV.

Boy did I get my wish, after a few more, I must admit, explicit messages back and forth, he asked “You’re staying in the …, aren’t you boy?” (I’m sorry, but the name of the hotel has slipped my mind). I was scared, so I tried to deflect the answer.

My heart was racing, I hoped that this stranger wouldn’t find out my location, and then I received it, the greatest message I’ve ever seen. “If you are, why don’t you come to room 1250, and show me just how badly you want it?”. And sent along with that text, was a photo of Aaron’s cock.

It was the most beautiful thing I had ever seen, at least 9 inches long, and as wide as a can of Coca-Cola. It was black, dark as the night, and (surprisingly) uncut. His bush was unlike anything I’d ever seen before, having never seen a black man naked. I could get the faintest hint of his ballsack from the photo, but I deeply needed to see more.

My fear, however, sobered me. I didn’t know if I could trust this guy. What if my family came back and I was gone? What if he did something to me? I stared at his dickpic for a couple minutes before deciding that it was too risky.

The moment that I gave up on Aaron’s cock, he sent me another text, this time a video. He was slowly, softly, massaging his cock, my cock twitched again, and I decided to throw caution to the wind.

I stood up, and quickly dressed myself, before grabbing the room key that had been left with me. As I walked to the elevator to make that treacherous climb of 2 floors, I texted my mother, making sure that they’d be gone for a few more hours.

I stood in the lift, my breathing heavy and ragged, the doors opened and I began traversing the corridors, searching for this daddy that I desperately needed.

Eventually I found his door, 1250, hesitantly I reached out my hand, I felt the wood of the door and stopped. I took a few deep breaths, then knocked the door.

I heard some rustling on the other side of the door, I thought about running, but then the door opened, and there he was, Aaron. He dwarfed me, I hadn’t had a huge growth spurt that would hit in my late teens, so I stood at about 5’5” staring up at him, who must’ve been about 6’6”.

My eyes traveled down his form, he was wearing the bathrobe of the hotel, clearly something he threw on to answer the door. I saw his slightly exposed pecs, my eyes traveled down further. I could see it, his bulge, my eyes expanded like a dry sponge being plunged into water.

He poked his head out of the doorway, and looked up and down the hallway, before stepping aside, letting me into his hotel room. I hurried inside and, having taken a few paces in, turned to face my host, I looked at his face as he turned around after hanging the do not disturb sign, closing the door, and locking it for good measure.

He was a handsome man, a short beard, white teeth, and deep brown eyes. He closed the distance between us and leaned down, cupping my chin with one finger and drawing my mouth up to meet his. I threw my arms around his neck, and he straightened up, lifting me off my feet. I wrapped my skinny legs around his waist as we made out, deeply and passionately.

I felt him take a few paces with me wrapped around him, then all of a sudden, I was falling, before softly landing on his hotel bed. He was back on me like a panther after a brief breath, his tongue dominating mine. I left his huge hands find the bottom hem of my t-shirt and begin lifting it. Deciding that he can’t do all the work, I begin sliding down my shorts (it was a very hot summer) and boxers, before kicking them off to a corner of the room, leaving my only in my socks.

Aaron stepped back, his soft, velvety voice purring the first words I’d heard from him “You want this?”. I hastily, and breathily, replied “Yes, yes I do”. Upon hearing my assent, Aaron gave me the finest show any man has ever put on, he deftly untied the belt of his bathrobe, and effortlessly shrugged it off. His body was now in full, naked, view. He was muscular, beautifully so, a perfectly proportioned man.

My eyes dropped like lead to the prize, the lure that had brought this foolish fish to the surface. It was huge, in person it had to have been damn near a foot long, so girthy as to beggar belief, and I finally saw a glimpse of that ballsack I’d been seeking. Two orbs the size of billiard balls hanging from his perfect torso.

My mouth fell open, I was in shock. I slid off the edge of the bed and stood against this man’s body. My hand reached out, I couldn’t even wrap my hand around his cock, but I started lazily playing with it, as I went on tip toes to kiss him again.

He walked to his bed and sat on the end, sending a silent message that was heard loud and clear. I stood before him as he sat and I kissed him, deeply. I broke the kiss and stayed about an inch from his lips for a second, patching myself up for what was to come, before I sank down to my knees before him.

His cock was, as already described, huge, in fact, it was bigger than my head. But while this was my first time cruising, it was far from my first time with a cock, though the friend that I’d turned into a fuck buddy definitely wasn’t as well equipped as Aaron was. So I knew how to make a man feel good.

I started with the lightest, most delicate of kisses to the tip of his cock, before my tongue slid out and began softly circling his massive head. But before I started sucking his cock, I needed to show his balls some love too.

I lifted his huge cock and set to work, I opened my mouth wide and took one of his balls into my mouth, it filled my entire mouth, but I sucked it like it was my last breath, I could hear Aaron’s soft moans as I began jerking his cock while I sucked. Eventually I detached myself from his balls and began sucking on the telephone pole in front of me.

I swear, I must’ve broken my jaw, but his cock was delicious, and it must’ve secreted a chemical that made time disappear, because eventually I felt a soft pull on my hair and heard him groan about how I’d make him cum down my throat.

I slowly stood up and said “Is there someway you can make this easier?” As I stood in front of him, my cock hard due to my time spent sucking.

He reached out to the bedside table and produced a funny looking bottle, he informed me that they were poppers, and explained how they worked.

I was so excited for getting fucked, that I practically leapt onto the bed next to him and presented my ass. As I faced away from him, I felt his huge fingers probing my asshole, wet and cold with lube. Eventually, after thorough preparation, he told me to take a whiff.

I smelled them, an insane sensation, but not as insane as my ass felt, as soon as I was ready, I felt him pressing against my hole. His giant cock creating surface tension, eventually pushing its way in, and eliciting a loud moan from me.

He started slowly, but his pace quickened, until he was fucking me like a machine, all I could think to do was moan and beg him for more: “Yes Daddy, please Daddy! More! YES!”

Time stopped making sense until I felt him slow down before pulling out, then I felt his warm cum coat my lower back. I peeled myself onto my side to find a puddle of cum where my cock had been resting as I got fucked.

After a few moments, Aaron let me use his shower to clean his cum and lube and sweat off my body. I came back out of his bathroom to him in his underwear, we made out for a bit longer before I stole away back to my hotel room, where I pretended that I’d been in bed all day.

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