I am pretty new to the world of man-to-man hook-ups. Though I had dated a few women over the years, nothing lasted. Maybe because I had always been bi-curious. For various reasons, I had resisted acting on this curiosity, instead satisfying the desire through online porn and playing with toys, like ring vibrators and dildos.
It wasn't until my early 50s that I acted upon it, back when Craigslist still carried personals. I ended up with two encounters with older guys - both were duds, with one guy who had ED and got pleasure just being naked with men (nothing wrong with that, but not my cup of tea) and the other just wanting mutual hand-jobs. While the latter ended up being the first time I held another man's cock, it was a letdown. I gave up.
At 58, I decided to try it again and created a profile on a hook-up site. On my profile, I identified myself as bi-curious, had little experience and only wanted NSA encounters, and listed my interests as ass play, anal, oral, and nipple play. I also posted some private pics.
Within hours of posting, I got a few hits, mostly from other bi-curious guys and bottoms. Then I got an IM from a guy who piqued my interest. He was 64, and was into the same things as me. His profile had no face pic, but did include a couple of his cock, which looked magnificent. He was 6' 3" and 240 lbs. He asked to see my private pics. I obliged.
A few minutes later, another message: "Hey, buddy, definitely interested. I can host if you'd like to play later today."
I replied that I was definitely interested, and reiterated that I had little experience - sharing details of my two previous encounters - but was looking for some mutual oral as the next step in my exploration. We agreed to meet later in the afternoon at his place, which was about a half-hour drive from mine.
As the appointed hour grew closer, I showered and headed out, hopeful this encounter would be more satisfying than the previous two.
He lived in a small Craftsman-style house on a cul-de-sac. I parked in the driveway and headed to the front door and rang the bell. Shortly, the door opened and I was greeted by a big, mountain of a man. He was clean-shaven, with a full head of dark hair that was graying at the sides. He was sockless, wearing jeans with an untucked flannel shirt that wasn't buttoned. I could see a hairy chest through the opening.
"C'mon in," he said. "I'm Terry."
"I'm Nick," I said, entering the house.
"You'll have to take your shoes off, Nick," he said. "I just refinished my flooring, and don't want any scuffs."
I took them off and followed him into the living room.
"Have a seat," he said, gesturing to a couch. "You want a drink? Water or something stronger?"
"I'm good," I said, sitting down on the couch, somewhat nervously.
He sat beside me, his right thigh touching my left thigh.
"So, not a lot of experience, huh," he said. "That's cool. You'll have a little more pretty soon."
"That's why I'm here," I said. "Like I said, I'm hoping to take that next step and try a little oral."
"Oh, I can help you with that," he said, with a low chuckle. "Why did you decide to take up my offer in particular? No other takers?"
"Well, your interests matched mine," I said. "There were others, but none floated my boat."
"Anything else?" he asked.
"What do you mean?" I responded.
"Well, you're a little guy," he said. "I'm nearly a foot bigger and probably outweigh you by 80 pounds or so. I've met a lot of guys like you and they tend to like more manly men. Does that sound like you, Nicky? Does your interest in porn lean towards daddies and bears, for example?"
