I lived the straight and narrow my entire life, but there was at least one hour a week where I did nothing but chase the thrill.
I had met Tom online one day when I was not just bored, but completely lost. The usual bullshit on these apps wasn't really cutting it for me, and I found myself straying from my typical desires. In some way, I suppose I was looking for myself - mid twenties professional, average body, nothing too crazy. Tom was a 52 year old gentleman who had no qualms about posting his preferences for a younger man, alongside a shirtless pic showing his sturdy, hairy frame. He looked strong, but safe, and I messaged him a simple "Hey man, looking good".
In due time, our pleasant conversation turned sexual. We exchanged our standard interests, and I sent him a shot of my cock. He returned the favour by sending me a picture of him laid out on a beach, completely naked and looking relaxed. For some reason, it struck me as - incredibly hot. He was clearly a man who was no stranger to the gym, but who's body had started to sag a little. The direct sunlight on him showed just how hairy he was, from his neck to his ankles. His uncut penis lay easily along his leg, looking about 8" or so from his nest of pubes to the tip. But more importantly I think, to me, was how comfortable he looked naked.
— Still there? — he messaged.
Despite never having been with an older guy, or even considered it before, I found myself drawn to this greying archetype. He sent me another picture of himself, this time seated in a club chair, wearing a white hotel robe that was open, exposing his long, limp cock. The angle of the shot was low, and gave Tom a lot of prominence. It brought out a craving in me to be down at his feet.
We texted back and forth, and before I closed the app, convincing myself that it was a one-off sexting session, Tom sent me a message would end up flipping my world.
— Come clean my condo naked —
Maybe it was the time of night, or the fact I had been touching myself during the conversation, but the weirdness of the concept actually turned me on. I could barely play through an idea of what would happen in my head before Tom sent me his location and asked if I was in or out.
Before I could second guess myself, I was in a cab hiding my hard on from the driver.
* * * * *
I showed up to Tom's condo, and was buzzed in by his concierge. I muttered his name, and the concierge simply responded with "Yes sir, he let me know you were coming,". I felt self conscious now, and strode to the elevator.
Walking down the dim hallway, I felt like I was marching to an uncertain fate, the patterns on the carpet seemed to be ominously guiding me to a simple, nondescript door. I knocked and waited.