A gay story: A First Time for Both
He looked to be in his early 20’s, maybe. Not much older than that. It was the two of us, and a woman who looked to be in her early 30’s or so in the Westin Hotel weight room. I was here for just three nights on business. I’m far from gay. Married, actually. To my beautiful wife Alyssa for twenty years now. With two children…a Senior and a Junior in High School.
I’ve been into weightlifting since my High School days myself, and always had an appreciation for the male form. Finding myself maybe not “romantically” interested in men…but certainly able to find a big muscly physique to not be too hard on the eyes. And this guy was built. Big shoulders. Abs that I could practically see underneath his Under Armor shirt. And veins like a road map up and down his arms.
The TV was on and he wasn’t wearing headphones so I did my best to strike up a little small talk between sets. “Close one for the Lakers…” I kinda said in his general direction. I knew nothing about sports, really. But I knew enough to know it was close.
“Yeah! We’ll see if they can pull it out…” He said back in my direction. Maybe he was pretty clueless himself. I got another set in and walked back to stand closer to the TV.
“What uh…are you uh…you here for, work?” I asked. Trying to take a stab at anything.
“Yeah, it’s like a…training, type of deal. Sit in a class all day and learn about taxes…” He laughed a little. “But it’s a fun little getaway to Denver so I’m not complaining too much.” He added. “You?”
“Yeah! Not a training though…more like, just….actual work. Consulting a bit on a bid we’re going to put in on a building here downtown.” I tried to stay vague. I didn’t think he’d really want to hear about any of it. And I could see he was turning his head to head back to his bench and get another set. I followed suit.
After we finished our sets we kind of both inched our way towards each other again, meeting between our machines. I motioned with my eyes to the woman behind him. She was dressed in tight little “Aurola” booty shorts and a white workout top. Very fit and so focused on her workout. I didn’t even have to say anything, he knew what I meant just with my eyes.
“Oh yeah.” He said, confidently. And then he got a little closer and lowered his voice, “So hot…”
“How am I supposed to get a workout in?” I said under my breath and laughed a bit. “She’s gotta be…what, ten years your senior?” I asked.
“Probably…I’m 24.” He said. I felt myself tingle a little.
Growing up, since I was quite young, I’d fantasized about much older men. And still to this day, my bisexual experiences remain just that. A fantasy. But I’ve realized I needed to stop making excuses and just go for it. If I get rejected, I get rejected. But I was tired of not finding out if I was into it or not. Now that I’m older though…I’ve found it fun to explore the other side of that fantasy. What if I could find someone younger who had my same thoughts at that age?
“Ten years your junior?” He asked, kind of boldly. I’d always wondered how old I looked.
“Close! 46.” I said, almost a little nervously. It looked like he was about to be done with his workout and I didn’t want to miss my shot. So I blurted out the first thing that came to mind.
“Hey, uh…” I paused for a second. “There was a problem when I checked in…the front desk gave me some coupon for the hotel restaurant…20% off or something, I’m not sure. But both of my meals while I’m here are with the client. You want it?” I offered.
He lit up a bit, “I mean, sure! Why not?” He picked up his water bottle. “Where should I….I mean, do you…”
I thought I knew what he was asking and interrupted him, rudely. “You about done? It’s in the room, we can just go grab it.”
I grabbed my room key and water bottle and we headed to the elevator. I pressed the button for floor 12, while checking the time on my phone. 5:30. I had to be to dinner by 7:00. What was my plan, here? I was at least getting him TO my room. Was I going to ask for his number? All the while, he was trying to make small talk with me in the elevator and I was barely able to think.
The elevator doors opened and I was starting to panic as we were walking down the hallway. My only plan was to change the conversation sexual. Quickly. As we were getting to door I said, “Man, she had a nice ass, huh?” Very directly. I wanted to see how he’d respond.
“Ass man?” He asked.
I nodded, “Oh yeah. I mean…I can appreciate it all, but if we’re picking…absolutely. You?”
“We’re one and the same.” He laughed a little.
I held the key card up to the door and it made the little beep. Pushing it open and he followed behind me. Before I looked for the coupon I pulled out my phone and pulled up a picture of my wife in a black bikini on the beach.
“This is my wife from a couple months ago…” I showed him with a smile. Handing him the phone so he could get a better look. I walked over to the table to grab the coupon and saw him scrolling through the pictures, holding it closer to his face.
“She’s hot..” He said softly. “Lucky man.” But he didn’t stop looking. And I knew what he was about to get to.
“Oh!” He said a little loudly. There it was. Alyssa riding me cowgirl from my perspective. And I loved that he didn’t look away.
“Here’s the coupon..” I handed it to him, trying to play it cool.
“Oh, uh…yeah, thanks. Here’s the…” He didn’t even finish the sentence as he tried to hand the phone back. But I didn’t take it. I actually set the coupon back down on the desk.
“Keep looking.” I said, almost sternly. He looked a little confused but just kind of held the phone back up towards his face in disbelief. Scrolling to the next picture of Alyssa bent over in doggy. My cock half way in her. And onto the next, of her on her knees in front of me with my manhood down her throat.
“She’s good at that…” I said softly, as he stared. “Like the older women, huh?” I asked, boldly.
“I um…yeah, kinda…” He said softly, not wanting to look me in the eye.
It was now or never. I reached over and softly gripped his cock through his shorts. Half expecting him to jump. Or run. Or make any sort of sound at all. But all that happened was that my palm got a handful of what it had always wanted to feel in it. Another man’s hard cock.
I couldn’t stop there though. My fingertips slid up his shorts and underneath the waist band. Down the front. His compression shorts were tight but I slid my left hand down, confidently gripping his manhood in my hand.
“I’d say you definitely like them…” I practically whispered in his ear from behind as I reached around him. I was practically melting. I couldn’t believe I was being so assertive. And he was definitely not going anywhere any time soon. My eagerness might have gotten the better of me as I confidently tugged on his gym shorts. Pulling down both pairs of shorts in one motion. I found myself dropping to my knees quickly, and encouraging him to turn around by gently turning his hips towards me.
I had exactly what I’d always dreamed about. And it seemed too easy to be true. A young, hard cock at my eye level. He was already standing as erect as he could be. Curving up and to the left. He was shaved bald. Not my preference, but it looked good on him. I eyed his beautiful tip for a brief second, but not too long. I didn’t want him to panic and leave. Already with a little shiny precum on it.