Disclaimer: This story contains scenes of sexuality between an older man (50+) and a younger man (21+). Due to the adult content, this story should not be read by anyone under the age of 18.
This story is the property of the author and may not be reproduced elsewhere without permission.
This is a true story. Names and locations have been changed to protect the identities of the individuals portrayed. More or less, these stories are accounts of events occurring between the author and an older man; my first, real older experience.
Feedback is always welcome and strongly encouraged.
Completely Discreet: Our First Meeting
by Young Pen Name
Since puberty, I have been interested in men. Many a night I would stay awake, locked away in my bedroom at home, browsing websites and chat rooms. I'd look at men, speak with men, and try to seduce men. I had spoken to a slew of random, anonymous men online, but never had the nerve to meet up with any.
Years passed. I harbored this desire deep inside myself, and kept it hidden from the girls I dated throughout high school. During my relationships, I had continued to notice men more than women. One day, I found myself single. I was no longer in any relationships, and felt a new wave of feeling wash over me. I dove right back into my old vices, and began speaking with gay men online once again. I joined several websites, hoping to find a man that would strike my fancy. Somewhere along the line, I developed a strong attraction towards older, more mature men. I can't say when or how, but it remains to this day.
One day, I met him. He was 51...29 years older than I was at the time. He described himself to me as a "middle-weight, slightly hairy, daddy." He didn't post a picture to the website we met through, and I didn't either. We were completely anonymous to each other. We spoke briefly online once, and then again, and then again. Slowly, I got to know him a bit better, and he got to know me. Each time we spoke, I felt more and more attracted to this unseen man. We worked our way into trading pictures of our penises, but I never saw his face. I wanted to meet him, but was far too nervous to suggest a meeting. One day, he did it for me.
He told me that he wanted to see me in person, and to meet him in a nearby mall. He suggested that we talk briefly, and if either of us were uncomfortable, we could leave at any time. No hard feelings. I reluctantly agreed. My heart was pounding inside my chest. I felt insanely nervous and anxious. On one hand, he was just some random guy who I met online and could be dangerous...but on the other hand, the things he said to me turned me on more than any other man had done to date. He told me when and where exactly he'd meet me, then he logged offline. I couldn't stand him up, so I got myself dressed, ready, and walked out the door.
My heart continued to pound away at the front of my chest during the ride over. I couldn't think straight. I couldn't even listen to any music on the ride over. My mind was a mess. We had agreed to meet on the roof of the smaller of two parking structures. It was noon on a hot, June day. I parked my car in the corner of the roof, turned my engine off, then waited nervously.
My mind raced, "What if he doesn't show up? What if he DOES show up? What do I say to him? Should I flirt with him? What if he tries to touch me? It's so bright outside...Why did we agree to meet at noon? Anyone could walk by and see us together! What if I disappoint him? What if I say something wrong to him?"
A red SUV drove up the ramp behind me, slowed down to a crawl. I kept my eyes locked on it, looking at it through my rear view mirror. It slowly pulled in next to my car, was put into park, and continued running. I looked over, and saw him. He smiled over at me through his sunglasses and his trimmed, greying mustache. He unrolled his window and motioned for me to do the same. I obliged, and he leaned out of the window a little.
"Daniel, right?" he called over to me.
I hesitated to answer at first. I swallowed hard, then replied, "...Yep! You're Red, right?"
He nodded to me. A moment of silence passed between us.
"Sh-Should...Do you want me to come over there?" I questioned, feeling my face become slightly flushed. All I could do was sit back and realize how stupid I must have sounded.
He nodded again, rolling his window back up. I took my seatbelt off, stepped out of my car, and walked over to the passenger side of his SUV. He unlocked the door, and motioned me inside. My heart still pounded away at my chest. I climbed up into his car, smiling nervously to him. I looked up and noticed him giving me a wide, pleased smile. A few more moments passed between us, then he spoke, breaking the silence.
"...Well, you're a lot cuter than any of the other guys I've met through the website, that's for sure." He smiled at me, still wearing his sunglasses, "How're you feeling, Dan?"
I nodded slowly, looking down at the dashboard, "I'm good...Nervous, but good," I laughed softly, "I've just never done anything like this before...I'm feeling pretty nervous."
Out of the corner of my eye, I could see him reaching for my leg. He patted my knee a few times, then moved a bit higher. He turned to me slightly.
He chuckled to himself, "...You're getting pretty hard for someone so nervous, Dan."
I looked down at my lap, noticing the bulge tucked away into the left pant leg of my jeans. His fingertips rubbed at my head slowly through the denim. I couldn't speak, and my heart was almost leaping out of my ribs. I just sat there, allowing him to rub at my young, erect cock.
"...If this is too much, I'll stop," he whispered.
I shook my head slowly, "No...I...don't mind."
I looked down at his lap. He was rubbing his own penis while groping at mine. The sight made me rock-solid. Red chuckled a little, unbuttoning his jeans.
"...Would you like to see it?" he whispered.
I nodded to him, remaining silent. He unzipped his jeans, reaching into his briefs and pulling his short, fat, erect cock out and stroking it. I could feel my face flushing again. The situation was becoming too much.
"...Would you like to touch it? he whispered again.
I laughed nervously, then nodded to him. Red reached over and took my hand, pulling it towards his lap and placing it over his penis. I wrapped my fingers around it and started stroking slowly. I could hear him beginning to moan.
"...I bet you want to taste it," he whispered, bucking his hips slowly as I stroked his hard cock.
I bit my lower lip, looking down into his lap for what felt like forever. I nodded to him. Without saying a word, he leaned back in the driver's seat. I leaned in, lowering my head to his lap. I could smell his musk, and almost taste his cock.
I looked up at him for a moment and said, "...What about mall cops? It's noon...they'll see us doing this together..."
He looked around the roof, turning back to me and saying, "I haven't seen one yet...I think we're okay..."
I hesitated for a moment, then leaned back in. I began to lick around his head with the tip of my tongue, collecting the taste bit by bit. I could hear him moaning, and could feel him quivering at my touch. I decided to dive right in, and wrapped my lips around his manhood, pressing it deep into my mouth. I felt Red as he grabbed the back of my head and slowly began to fuck my young, eager mouth.
"Ohh, yes...Oh, Daniel..." he began to moan.
I moaned softly, muffled by the hard cock in between my lips. He kept pressing against me, shoving it deeper and deeper into my mouth. I could feel it throbbing inside me. I felt his fingers running though my short, brown hair. His right hand crept down my back, clasping firmly over my ass.
My mind continued to race, but thought brand new thoughts, "I'm finally doing it. I'm sucking an older man's cock. I'm so excited right now. I hope he asks me to go home with him. I want to feel this dick inside me. I want to taste his cum. I want Red to shoot his thick load down my throat. Please cum, Red...Please..."
"Mmnn...wait, wait..." I heard him moan.
I pulled away from his lap, popping his dick from my mouth, "Mmn! What's wrong?"
He chuckled softly, "If you keep that up, I'll cum."
I grinned wickedly up to him, feeling a new personality take control of my actions, "...I want you to cum. All down my throat."
It excited him. I could tell. He ran his hand across my face, then pushed me back towards the passenger side of his car.
"Give me your phone," he demanded.
I obliged, handing it to him. He programmed his number into my contacts list, then handed it back. He tucked his hard-on back into his jeans, and smirked to me.
"Call me tomorrow night. You can come over to my place. We'll finish this up then. If you want my cum, I'll give it to you, Daniel."
To be continued...