It happened four years ago, I was living in a single bedroom apartment and going to college. I had been curious about having another man's cock in my ass. I spent hours daily masturbating to gay porn. I had purchased some toys to accentuate my masturbation experience. It always helped me shoot cum further. I started small with anal beads, pulling them out one by one when I was climaxing. Soon I moved to dildos. I practiced giving oral on them and used them in my ass. I moved into bigger dildos and ones I could stick on my shower wall so I could jerk off and imagine getting fucked.

I got bolder with my masturbation. Going for runs, I would go to heavily wooded parks and go into the woods pull my shorts down and jerk off until I cum. I really enjoyed masturbating and worked on my flexibility because I wanted to suck my own cock. I got close but was only able to barely lick my tip. I did shoot loads of cum into my mouth and swallowed. Of course I did do some of my masturbation online. I enjoyed having an audience and got several offers. I started doing shows or posting videos of myself daily.

One evening I was reading some of the comments on my posted videos. A comment from one guy caught my attention. He asked if he had seen me running through a park. He described what I was wearing and what time he saw me. At first, I was shocked and it kind of creeped me out. After it sunk in, I replied to him saying yes and flirted asking for a picture of him. Within minutes he replied and we ended up chatting on y***o. His name was Mike, he was 37...almost 20 years older than me. He was gay in an open relationship, he was a few inches taller than me, in good shape, top, and hung ( he was nine inches ). I was very intrigued. We talked in depth about what each other's desires. I was 18, I had a nice slim build, not hung...just 6.5 inches, smooth, and a very curious bottom. It seemed like a good match except for his age. But the more we talked the better I felt. Mike even got me to call him and we talked on the phone. After a few hours I agreed to meet him. Mike was very serious that I not set him up and leave him hanging.

Mike laid out everything in great detail. I was to be shaved smooth all over, given myself an enema, prelube my ass, condoms had to be supplied by me or just bareback...Mike preference but was willing for our first meeting, and I had to be naked at the door when he showed up. I agreed to do it all and I was very excited and nervous. As I waited for Mike, I couldn't believe it was finally going to happen. I nervously shook pacing around my apartment naked. When I heard a light knock on my door,I jumped a foot. I opened the door and Mike came in. He was very happy to see me. We shook hands and sat on the couch. Mike started running my cock with his hand. It felt electric, I was shaking. He took my hands and placed it over the buldge in his pants. He asked me to unzip him. I slid my hand down his pants. Before long we were naked in my bedroom. I asked that he take me missionary style. I laid back and Mike fingered my ass. It felt so good. He used two then three fingers. I was rubbing myself while he worked on me. I opened a condom and was about to put it on Mike. He took it away and tossed it on the floor promising to pull out before he cummed. I was so excited I didn't care. I put lube on his cock. Mike moved in as I lifted my legs up. He pressed against me and I resisted a little. Then he pushed into me. I gasped how big it felt. He pushed further and I placed a hand on his chest asking to go slow. He pulled back so I could catch my breath. Then Mike pressed hard into me. I started masturbating while he pumped in and out of me. The deeper he went the better it felt, it was painful and exciting. The slurpy sounds of him pulling out and the slapping of his balls against my ass cheeks. Mike was going at smooth pace while I masturbated furiously until I shot my cum over my chest and abdomen. Mike ran a finger through it and had my luck it off for him. Mike started drilling harder into me. After I climaxed the pain was more noticeable. I was sweating and grunting louder every time he plunged into me. Mike felt enormous. I was struggling to catch my breath, our bodies slapping into each other. It started to burn. I pleaded with him to stop. Mike slid out slowly. I breathed a heavy sigh of relief. I lowered my legs and Mike straddled them. I gently rubbed Mike with both hands. Playing with his balls caressing every inch of his manhood. Mike was close. He moved forward pinning it to arms under his legs. He leaned over me and told me to open up. I accidentally bit down on him and he flinched pulling back a little. Then he forced his cock into my mouth. I could taste my ass and the lube. It didn't taste good but in the heat of the moment I went for it. Mike slowly fucked my mouth until his warm goo filled my mouth. Mike pinched my nose which made me swallowed. He filled my mouth twice and I was forced to take it all down.

Mike looked satisfied. I had tears rolling out of my eyes and salvia, cum,lube rolling out the side of my mouth. Mike got off me and we took a shower. He let me wash him up. As we dried up, Mike was hard again. He sat at the edge of the bed and let me give him oral on my knees. The practice with the dildo paid off. I almost could swallow his entire cock. Mike tried to help forcing my head down on him but it resulted with gagging and a little throw up. He was close and had me get on all fours on the bed. He stood behind me and slapping my ass cheeks with himself. Then he found his target and put his hands on my hips pullpng himself into me. I tried to pull away. I had to bury my face into my pillows screaming in pain. Mike didn't top. It hurt so bad,it felt like he was ripping me apart as he pulled back out of me. Then he grunted as he unloaded into me. It helped with the friction a little. Mike pulled out. I collasped on my side curled up.

Mike put his clothes on and told me he'd be in touch. It took me two weeks to recover and actually be able to sit down without pain or medication. Sure enough Mike contacted me a few days later wanting to hook up.