A couple of years ago, after decades of being bi-curious, I finally acted and visited a nearby park trail that was known to be a hangout for men seeking anonymous hook-ups with other men.
I was walking the trail when a younger guy, maybe half my 60 years, approached me and asked, "are you looking for some naked fun?"
Startled by his bluntness, I just nodded.
"Follow me."
He led me down a narrow path to a little clearing, where there was a blanket, some towels and a cooler. He removed his t-shirt and sweats and got down on the blanket. Nervously, I removed my shorts and t-shirt, glancing around to make sure nobody else was around. Not sure what to do, I sat down next to him. He leaned over and took my dick in his mouth and immediately went to work.
Fuck he was good. He was gently fondling my balls, as he sucked and licked my dick, which he managed to get good and hard in seconds. He then took my hand and put it on his dick. I started stroking it and felt it begin to harden. Embarrassingly, I lasted about a minute before I blew my load, which he eagerly swallowed. He lifted his head and smiled.
I leaned down and took his dick in my mouth. It was exactly like the descriptions I read in so many porn stories: spongy and hard at the same time, with a slight scent of sweat. I alternated between licking and sucking his mushroom head. I started to go deeper down, but couldn't get much in my mouth before I started gagging a bit.
"First timer, aren't you?"
I stopped.
"Is it that obvious?" I asked, somewhat defensively.
"The teeth and gagging are dead giveaways."
"Sorry," I said.
"No worries. I'll find someone on the trail."
And that was it: my first experience in all its unsatisfying glory. I got dressed and left. But as I walked back home, I realized how much I enjoyed that little taste and vowed to get more. And then the damn pandemic hit. Hook-ups were too risky.
Fast forward to today, and the latest variant is in retreat and restrictions are being relaxed. I placed a "bi-curious" profile on an adult hookup site and began scanning other profiles. Immediately I was getting lots of guys checking out my profile -- probably because I was new -- but no follow-ups. I was too nervous to reach out to others.
Finally, the following day, I got an email. It was from an older gay guy, aged 67. His profile listed him at 5' 11" and 210 lbs., far bigger and beefier than my 5' 6" 145 lb. frame. The only photo was a dick shot, which looked very tasty.
"Your profile says you're inexperienced. I can help you with that."
"Thanks," I replied. "I'd be interested in meeting. But in public somewhere first, just to see if there's a connection."
"Cool. How about 4 pm tomorrow at O'Hare's? It's near my place. I'll be wearing a black denim shirt and a red cap."
"See you then," I replied.
The following day, I was a bundle of nervous energy. I googled the bar, downloaded directions and headed out. Fortunately, there was on-street parking with no restrictions near the bar. I walked in and looked around. It was clearly a gay bar. I saw my connection in a booth near the back. I waved and walked towards him.
"I'm Dan," he said, extending his hand.
"Cam," I replied, shaking his hand. I moved to sit down opposite him.
"Sit here, beside me," he said, standing up.
I slid into the booth and sat down beside me, his leg touching mine. He was good looking guy, clean shaven with longish gray hair. He was broadly built.
"Would you like a beer? I recommend this IPA", he said, pointing to his glass.
"Sure, thanks," I said.
He motioned the bartender, who brought one over.
"Tell me about yourself. Just how inexperienced are you and what are you looking to experience?"
"Um, well, I was with one guy," I said. "A couple of years ago, before the plague. He gave me a blowjob but when I tried to return the favor it didn't go well. As for what I'm looking for, I dunno, oral anyway."
"I see. Well, let me ask you some questions if you don't mind. Maybe together we can determine how far you're willing to go."
"Sure," I replied.
Do you watch gay porn and jerk off to it?"
"All the time," I admitted.
"What kind of videos do you watch. Blow jobs, fucking?"
"Both," I said. "Ideally in the same video."
"What type of men do you like to watch? Big...small...young...old?"
"Um, well, I kinda like guys around my age or older and, um, big and small," I said.
"So, a bigger top and a smaller bottom I assume? Do you fantasize about being one of the men?"
"Yeah, most of the time," I said. "No, actually all of the time."
"Which one?"
"The bottom," I confided.
"Given how small you are, no surprise there. What about a threesome or more?"
"Yes, I've fantasized about that, too," I said.
"Do you play with toys?"
All these questions. As I was answering them, though, I could feel my dick stirring. It was oddly turning me on to reveal myself to this stranger. But I could also feel myself starting to sweat a little nervously. I took off my jacket and took a big gulp of beer.
"Yes, I started out with a starter butt plug kit and gradually moved up to a realistic dildo," I said.
"How does it feel when you insert the dildo in your ass?"
"It's a bit uncomfortable at first," I said. "But when it's almost all the way in, the feeling is so good. I sometimes shiver a bit. It also feels amazing when I pull it out, though the empty feeling is weird at first."
"And I bet you wonder what if feels to have someone cum in your ass."
I didn't respond. I didn't have to -- he knew the answer. Though with all the STDs around, it worried me.
He reached down and felt my now hard dick, and smiled slightly.
"This is turning you on, I see. Any other things?"
"Uhh, yeah," I said, feeling my face redden. "I have an enema kit."