Ready for the Real Thing?

The flight to Toronto gave me plenty of time to reflect on how my online relationship with Jason had developed.

I had started chatting with Jason about three months earlier. He was safely located hundreds of miles away in Toronto. An older guy, looking for some cyber fun. Never crude, he always played the gentle, older uncle type.

I never let on how limited my experience really was. I had been with few guys, mostly jerking each other off. I had given a few blowjobs but was far from an expert. I'd had one anal experience....and that had been very uncomfortable. But I was very horny, so I played along.

Our "encounters" usaully went something like this...

As we entered Jason's apartment, he would lead me to his living room. After a few drinks he would start slipping his hand between my thighs, slowly working his way up to my crotch, massaging me to a nice hard erection. I was always too intoxicated to resist & before I realized what was going on we were in the bedroom....naked. I inevitably ended up on my knees with his thick 9" cock in my mouth. Always careful not to be too forceful, Jason would let me take only as much as I could handle. He would gently pull me to my feet and lead me to his bed. I could almost feel his heavy breath on my neck as he described how he would gently probe my tight little ass with his finger....lubricating it gently....probing...slipping it in.

Our encounters always ended with the full length of Jason's thick cock buried deep inside me...filling me with cum....and me panting for more.....

After our first few online encounters, Jason & I began corresponding regularly by email. We traded pictures and I soon realized that he had not been exaggerating how big his cock really. My mouth watered at the sight of it. Jason felt the same way about my pictures; in almost every email he sent he described how hard he got looking at my tight, smooth little backside. Our sessions got more intense each time we chatted.

Jason begged me to come to Toronto for a visit. I hesitated at first, not wanting to disappoint him with my true inexperience. Deep down though, I wanted a real meeting as badly as him & eventually agreed. Had I made the right decision?

I recognized Jason instantly when he met me. He was a bit taller than I pictured, about 6'2", well tanned, a very fit, attractive 50 year old. I wondered if he found me attractive as well.

The drive to his apartment was pretty uneventful. We chatted about the drive, traffic, the weather. I felt comfortable & glad I had decided to come. That began to change as we entered the elevator from the parkade. There was no turning back now. As the elevator doors slid closed, Jason leaned over and kissed me fully on the lips. My heart was pounding! I closed my eyes and let his tongue explore my mouth...it felt wonderful!

Jason pulled away as the elevator stopped and led me to his apartment.
We stepped inside. It was quite dark, all the curtains appeared to be drawn.

Jason kissed me again, this time pulling me tightly towards him. His lips were warm & soft, his tongue searched deep inside my mouth. His hands found their way easily inside my loose fitting jeans, slowly massaging first my firm backside, then slowly working their way to my already throbbing cock. I could feel my jeans falling to the floor and reached down to undo his pants. I fumbled with the snap, but was able to eventually undo his pants and slip my hands under the waist band of his briefs.

I pulled away from Jason's embrace & dropped to my knees. I wanted to see first hand the cock, whose pictures I had so frequently masturbated over, up close. As Jasons briefs slid to the floor, I gasped at the size of his cock. It was much bigger than I had imagined. Thick and getting hard before my eyes, the head was already huge.

I wrapped my hands around Jason's cock...they seemed so tiny now....and started stroking it slowly. As I leaned forward for my first taste, I could feel Jason's hands gently stroking my head. I let the huge head slide in & out of my mouth, gradually taking about half of the full length of his enormous erection. I was afraid I would choke, but was able to go a bit deeper with each stroke. Before long my head was bobbing up and down as I tried to swallow the full length.

I'm not sure how long I had been sucking when Jason pulled me to my feet. He led me to his bedroom. We stripped off our shirts and climbed between the sheets. His naked body felt incredible as he pressed it against me. His hands roamed freely over me as he held me in long embrace. His warm hands had my hard cock throbbing as he stroked it gently. He began to reach deeper between my legs, spreading them gently so his fingers could reach my asshole. He rubbed it gently. It felt so good!

I was totally relaxed as Jason turned me over onto my stomach. He propped me up on some pillows, so I was on my knees, my head resting on the bed. As he spread my legs I could feel the warmth of his tongue probing my anus. He circled the outside for several moments before working it deep inside me. Next, I could feel his finger inside me. Slowly going deeper. Then making deep strokes inside me.

I had never imagined how pleasurable any of this could feel. Jason had very skillfully gotten me to a point where I was begging for more. My asshole was lubricated, slippery, and willing. I had imagined fearing the entry of a cock the size of his...now I wanted it more than anything!

I could feel Jason's hot breath on my neck as he slipped in behind me. The swollen head of his cock was now pressing against my wating asshole....slowly but surely slipping inside me. I let out a gasp and Jason paused when the head was fully in. As I started to breath again Jason began working his cock deeper inside me.

Jason began whispering what a good boy I was. I felt as if my whole insides were being filled by Jason's enormous cock, but I wanted desperately to please him.

Jason worked it in as far as it would go, then began making long deep strokes. His grip tightened, his breathing got deeper, and the strokes came harder and faster. I was having difficulty breathing as Jason's weight forced my face into the bed. Suddenly, as I was beginnning to gasp for air, I felt a warm fluid spreading inside me. Jason's grip loosened as his hot cum filled my ass...his cock sliding freely inside me now. His panting was heavy as he continued his strokes, squeezing every last drop of his cum into me.

We fell asleep exhausted.... and when I awoke I immedietly begged Jason for more.