I have decided to write some of my actual, non-fiction gay hookup experiences, as well as some fiction fantasies that I am into. This is a true story. It is not chronologically my first hookup. These will be submitted out of order and will be interspersed with fiction as well.
Around 2008...
I was working for a few weeks in downtown Nashville, TN (I am from Los Angeles), and staying in a hotel there for the duration. One night I posted a craigslist ad for an m4m hookup and got a response from a gentleman that lived relatively close to my hotel. His photos showed a rugged face with a big jaw, not handsome but attractive due to his overabundant masculinity. He was the type of guy that never could get rid of the five o'clock shadow. He was a white male probably in his late forties (I don't remember) and had a masculine physique but wasn't "worked out" at all. His response stated that he was a top (yay!) and his cock was 7.5" cut and nice and thick.
I emailed him and he mentioned that he lived in a loft downtown and that I could come over. Soon, I was on the phone with him listening to his sultry, husky older man voice easily persuading me to walk the couple of blocks to his place to at least come and check out his awesome steam shower.
At the time I was about 24, 5'10" and 155-160 pounds. I am white, with freckles, blue eyes, and ash brown hair. I've always been kind of skinny though at the time I had been hitting the gym two or three times a week so I was in pretty good shape. My cock is really nice and straight and pretty, but it's only about 5" long fully erect. I am bi and closeted. I only periodically hookup with men. I have had a few male partners in my life but I wouldn't call myself skilled. Most were one night stands, though I had a couple of partners that I hooked up with 2-3 times. Then, I was a very inexperienced oral lover that had spent some time alone exploring my anus but had yet to bottom for anyone. Now at 31 I am a very giving versatile/bottom with a weakness for big dicks, but especially big dicked tops.
I walked in the cold night to the street address he gave me, an old brick building. There was no traffic and there were quite a few unmarked doors at the ground level of his building. It was very confusing, so I called him and he came down to open the front door for me. This was our first time seeing each other and his pictures fairly represented the real deal. He was taller than me and a pretty burly guy in person. He wore a T-shirt and some pajama pants.
I followed him up a few flights of stairs and found myself in a beautiful renovated loft that took up easily half of the penthouse of the building. It was really impressive. Clearly he was a very successful man. There was a bar stocked with all kinds of liquor. I remember that I requested a Jack and Coke and he had the same. We were both nervous (I was more nervous than him) and the tumblers of sweet liquor helped take the edge off. We made small talk on his couch as we sipped our drinks. He explained that he owned a high-end art gallery in downtown that did a brisk business with the wealthier residents of Nashville. I told him about my job working in stage setup and he politely pretended to be interested.
As we finished, he took my hand and stood up. He leaned in and kissed me. We stood for a few moments savoring the kiss, and I explored his mouth with my tongue. He let me do what I wanted but somehow left me wanting more. The kiss broke breathlessly he led me on. I was in awe as he gave me a little tour of the vast main living area filled with expensive furniture, the kitchen off to one side, the huge windows that faced the street below.
Finally we stepped into his bedroom, with a huge elevated four poster bed with thin translucent cloth curtains draped on each side. He let me take in the enormity of his bed for a silent moment, then turned to me and pulled me to him to deliver a much more aggressive kiss. He stripped me naked in seconds and caressed my body while burying his face in my neck. He was intoxicated with desire so I let him stand behind me to take me in and savored his attention as my cock stiffened. It felt so good to have his hot breath on my neck and in my ear, and his big man's hands roaming around my torso. I could feel his growing erection through his thin pants, pressing against my naked bottom. I turned to face him again and kissed him more, letting my tongue dance with his.
But he pulled away. He walked around to the nightstand to grab a small remote which he used to dim the lights. He pulled his shirt over his head and threw it on the floor, then hopped on the bed, leaning back against the mound of pillows at the head of the bed. He gazed at me with a little smile on his face as if waiting for me to make the next move.
Well I read that non-verbal "suck my big cock" cue loud and clear and eagerly crawled up onto the bed. I briefly caressed his cock through the front of his pants then impatiently pulled his pants down and off. I laid between his spread legs to inspect his manhood more closely. As is to be expected with any online hookup, his cock wasn't really 7.5" long. It was probably in the 6.5"-7" range, but he definitely wasn't lying about it being thick. His shaft was narrower at the base and gradually got thicker as it approached the tip, ending in a large mushroom head that was even thicker and fatter than the shaft. It wasn't exactly what he had represented in his email, but it was actually really nice and I liked his huge shiny purple cock head. As I gazed at his dick he began precumming as it reached full erection. I took the base of his shaft in my hand and a big drop of clear liquid grew at the tip of his cock. When it was about to fall I licked it off. It was very mild and a bit salty. Like all precum I suppose. Another drop started growing right away and when it fell I watched it roll down the underside of his shaft to the top of my thumb. Then I started sucking his cock. I wrapped my lips around the crest of his purple glans because I wanted to know how it felt in my mouth. It felt wide, and good. :) My tongue was pressed up against his urethra and I tasted the precum as it issued from his dick, then swirled my tongue around and around his cockhead as I held it inside my mouth. He liked that a lot, moaning in appreciation. I bobbed my hand in sync with my head, trying to fit a bit more of his dick in my mouth each time. Soon I had at least two thirds of his fat manhood sliding in and out of my mouth, and I felt like I had achieved something impressive! I was deep throating!
Of course I wasn't really deep throating him but at the time I felt like an accomplished little cocksucker. His dick was pretty big! I sucked his balls and rolled them on my tongue. I ran my tongue and lips up and down his shaft, then enjoyed that big fat mushroom in my mouth over and over again. Once I had slobbered on his dick for a good while he stopped me and laid me down on the bed, sucking my entire cock down his throat on the first try. He spent a few minutes going down on me but stopped quickly.
He obviously had other things on his mind. He asked if I had ever bottomed (No) and if I wanted to (No thanks). He understood my apprehension and promised he wouldn't. He pulled out a big bottle of some oil-based lube and had me lay face down with my legs together, then slathered lube all over my butt and between the tops of my legs. He mounted me and slid his cock between my legs, slowly gyrating his dick back and forth between the tops of my thighs and getting really into it. A few times he came very close to my anus and I told him not to surprise me. I could tell he wanted to fuck my ass SO BADLY but I had never done it before and I wasn't ready. He went faster, slamming that shaft between my legs as I lay there listening to him grunt. He asked if I wanted to taste his cum (eww, no) and I told him to cum all over my chest, so he pulled out and mounted me, jerking off his hot load all over my chest.
He collapsed on the bed and after a few minutes of recuperation and toweling of cum I asked him about the steam shower he mentioned. He seemed a bit put off by my request but led me into the bathroom to a massive steam shower room with a whole bunch of nozzles. He got it started and we both stood there naked and still covered in lube as the shower filled up with billowing clouds of steam. He kissed me and leaned me back against the wall, getting on his knees with my cock in his mouth. At this point he really did surprise me: as he sucked my dick, he slid one of his fingers up and down my ass crack to lube it up then without hesitation slipped it straight into my asshole. He must have found my prostate right away because I felt weak in the knees and in about 2 seconds started cumming. He felt my load approaching and jerked my cum all over his chest and onto the floor of the shower. I sighed after my intense orgasm, and I remember it felt really weird and good as he gently withdrew his finger from my ass.
We chatted for a little bit after we dried off and dressed, and I left. Thinking back on it now, I wish I had let him fuck me. He obviously didn't want to cause me pain. He was obviously a very skilled top and the size and shape of his dick would have felt really good inside me, rubbing against my prostate.
Hope you enjoyed my Nashville story. :) Please email me and tell me what you think.