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."
"Did you use it before you came here?"
I nodded. Another small smile crept across his face.
"Well, that's an indication of what you're willing to experience I'd say."
I looked down, and nodded again.
"Well, we've established that you're a bottom. You also seem a little timid. Not all bottoms are submissive, but you are, aren't you?"
"I think so," I said. "I've never been in a situation to test that out."
"Married?"
"Nope, never got married," I said. "Dated a few women but it just never worked out."
"Maybe there's reason, one that's pretty obvious to me. And probably to you, even if you never fully came to grips with it. But here you are, no longer able to resist the desires you've repressed for so long. You can't deny them anymore."
"No," I said quietly.
"Undo your pants and show me your cock."
"Here?" I asked, nervously.
"Do it."
I did as I was told, reached in and pulled my dick out.
"Stroke it for me."
I began stroking my dick. I kept glancing around, wondering if anyone saw what was happening.
Dan's smartphone pinged. He pulled it out, read the text and responded.
"We're going to my place," he said. "A couple of my friends are waiting there."
He got up, left $20 on the table and motioned me to follow him. I quickly did up my pants, slid out of the booth, and followed him out of the bar and into the sunshine, my erection visible for all to see through my pants.
"My place is a few of blocks away."
We didn't say a word on the 10-minute walk. Fortunately, I got soft again, avoiding embarrassment. His place was a brick townhouse. It looked expensive from the outside. We walked up the steps into his place. He kicked off his shoes in the foyer, hung up his jacket and I followed suit. He looked at me with an almost expressionless face. He reached over, grabbed the bottom of my hoodie and t-shirt and pulled them up and off me. Then he unbuckled my belt and pulled my pants and underwear down in one motion. I stepped out of them, and then pushed my socks off.
I was naked.
He grabbed my shoulders gently and turned me around. He rubbed his hand on my ass and then slowly up my back, before moving it back down again and rubbing my ass cheeks. My dick started stirring again. He leaned in and I could feel his breath on my shoulders.
"Tonight's the night. You'll never be the same. You'll be craving cock."
He grabbed my arm and led me into the living room. As he said, two other guys were there, both naked.
"Meet my two buddies, Greg and Phil," he said, pointing to each one.
Greg was about Dan's height, but quite trim, balding, and also looked to be in his 60s. His dick looked disproportionately long, but not thick. He was grinning in anticipation. Phil was in the same age range, but shorter, maybe 5' 9", and stocky and hairy. His head was shaved, and he had a huge, thick moustache. His dick was much stubbier than Greg's.
"We take a great deal of pleasure in awakening repressed 'bi-curious' men, especially if they're submissive little ones," Dan said. "I thought I had you pegged the moment you walked into the bar and your answers to my questions confirmed it. You just opened up and let it all out. It's why you're here now, why you came willingly with a stranger to his home where you knew others waited."