I had my first experience with another man at the age of 19. It had always been a thought in my mind, but I never really felt compelled to try it until I came across a local gay dating website. I met a guy through the chat room and we ended up watching porn and masturbating together. I sucked his dick for a few minutes, but we came while watching each other work our shafts. It was exciting, but didn't live up to the experiences I had with my girlfriends at the time. I knew I wanted to experience more.
I hooked up with several more guys online, and became pretty sufficient at using my mouth for the pleasure of my fellow man. I loved it; the feel of a smooth cock head squeezing into my throat and the continuous hardening until it finally exploded over my tongue. It made my heart race to hear another man groaning as I brought him to ecstasy, knowing that I controlled his pleasure. It gave me a sense of power while also degrading me. I felt so dirty on my knees with cum and saliva dripping from the corners of my lips. Then there was the difference between getting a blowjob from my high school girlfriends and getting one from an experienced man. The girls may have had enthusiasm and an urge to please going for them, but a man knows what a man wants. I was loving life, but I was waiting to go one step further. I wanted to get fucked.
Nowadays I'm pretty heavyset, but around the time I hit twenty I was looking alright. Oh I was overweight, but beneath my gut was a pretty impressive set of muscles. I'm 6'3 and was weighing in at about 270. I had the good fortune to take to weightlifting, and had large pecs and tight swollen biceps. I basically looked like an out of shape linebacker. With my shaggy brown hair and gray eyes I cut a nice figure (or at least I like to think I did)
Through the site I had been exchanging emails with Tom for a few weeks, discussing our interests and sexual fantasies. We decided to meet for coffee one night, but as I drove up, the place was closed. He pulled up beside me and I jumped into his car. We debated going to his place but his straight roommate had gotten home, making any potential fun a bit awkward. We ended up pulling into a secluded lot and making out for awhile. He was even bigger than me; taller by an inch and a good bit heavier, but he was cute and had thick, kissable lips. As our tongues danced between our lips I placed my hand on his thigh and gave it a squeeze. Sliding up his leg I ran into something in his pocket. Except isn't a pocket on the outside of your leg? And no pocket goes this far down.....
I gasped and my hand shot to his zipper. I had to see what I had stumbled upon. As I yanked his fly open and began fishing out the his thick root from it's base, I was astonished. I could barely fit my very large hand around it and the more I pulled the longer it seemed. Finally I freed this giant member and in the moonlight I could tell that it was the largest I had ever seen. Possibly even larger than any in my vast porn collection. At least ten inches long and as thick as a fat baby's upper leg, it was still half flaccid. I didn't waste any time and dove face first onto his lap. I fought to get it into my throat, but in the tight confines of the car I couldn't maneuver very well. After some neck breaking gymnastics and a heavily tested gag reflex I had worked my way down about half the length,
His hand was massaging my balls through my jeans and he began working my pants over my backside, which was pointed out the window. Thankfully no one drove by and saw, and he managed to get his hand under my waistband. There was a sudden pressure from behind and I felt his massive finger pushing it's way into my ass. At first I winced from the violation, but I quickly came to want more and pushed back against Tom's palm. As the resistance gave way I felt a rush, and his finger was deep in me with a slight pop. Lust overtook me and I started to piston my head up and down, impaling myself further onto him. Within minutes I had gained a few more inches. I felt like his inhuman shaft was going to reach my stomach. With every last bit of willpower to think straight I had left, I fought the urge to choke and forced myself even lower onto that magnificent cock. As I struggled and my throat constricted, I felt Tom add another finger to my stretched anus. He was moaning and pushing up into my mouth, his balls radiating heat and beginning to swell.