In the first chapter, I describe my first adventures with anal masturbation and my first experience with a man.
As I said, I thought I was just experimenting and that, now that I had tried it, I wouldn’t have an interest in going any further. As you can guess, I was dead wrong, or I wouldn’t be back for chapter 2. As I mentioned before, these stories are as close to the truth as I can remember.
Almost a year went by and my interest in anal sex and sex with men had waned, I believe it was because I was getting steady sex with a girl I was dating during my last year at college. After graduation, I moved to a big city and found myself alone with plenty of time to cruise the internet and yet again, I started chatting with men online. I believed this was just because women were so hard to find on the internet.
I met a guy online and we chatted for a while until we agreed to meet in person. I went over to his place and we hung out for a while and had a few beers. I had gotten over my nervousness after the second beer when he started to fondle my crotch. He unbuckled my belt and reached inside my jeans and started stroking my cock. This made me bolder and I reached over and did the same for him. I could feel his erection was about an inch longer than my 6.5 inches and thicker too. I couldn’t wait to see what felt like a magnificent tool. I got on my knees and pulled his shorts down and out sprang a gorgeous, hard throbbing cock. He already had a bead of precum on the tip. I reached a finger over and took the salty bead into my mouth. I tasted wonderful. I leaned forward and started licking the shaft of his dick. I made my way up to the head and took it in my mouth. I started stroking his cock while my tongue swirled around the head. He started to moan and grabbed my head pushing me down on his cock; I gagged, but adjusted to having this huge cock in my throat. I was jerking off my own cock while hungrily devouring his. I could tell we were both about to come when he pushed me away. He had me stand up and took my clothes off. I stood there naked while he ground his cock against mine jerking us both in his hand. He took me by the hand to his bed and pushed me down on my back. He climbed on top of and continued to rub his cock against mine until we were both getting very aroused and were bucking our hips against each other. He moved down and took the head of my cock in his mouth and started sucking hard while jerking me off, then before I knew what was happening, he swung my legs up exposing my ass and his face went down. I felt his tongue licking my ass while he slowly stroked my cock. What an amazing sensation! I had never had any of the girls I slept with even get close to doing this to me. His tongue started probing my asshole getting all wet, then I felt his other hand start to gently finger me. Before I knew it, his finger was inside me. (Those of you that read chapter 1 will know that I had never had anything in my ass except my own finger and a dildo I had bought online.) After a few minutes of rimming and fingering my ass, he looks up and with pure lust, says: “I want to fuck you.” I was so turned on by then that I said ok. He stood up went to the nightstand and pulled out a condom and a bottle of lube. He poured some on his cock and started stroking, then slipped the condom on. He then squirted lube on my ass and fingered it to get the lube up inside. He said he wanted me on top, and laid down on the bed. I straddled him while he jerked off my cock then pointed the tip of his cock towards my ass. I felt him probe as he found the proper spot, then gently push upwards towards me. The head penetrated me and moved further up. At this point I felt a searing pain and withdrew. He was very gentle and asked if I was ok. I said it hurt, but that I wanted to try again. After a few seconds, the pain had subsided and I again moved myself down on his cock. This time, the pain was bearable and I felt his throbbing dick moving into me slowly inch by inch. Before I knew it, he had hit my prostate making my cock jump and seem to grow another inch. I had taken all 7.5 inches of him inside me and was loving it. I slowly began to grind myself against him and gently rode up and down. He was stroking my cock making me more adventurous and I started moving faster. I knew I wouldn’t last long with this extreme pleasure and I pushed his hand away. I continued to ride his cock until he grabbed my hips and stared thrusting my ass. He was moaning and grunting, then said:” I’m gonna cum!” His hand quickly found my cock and gave me a fe good tugs at which point I erupted in one of the largest cums of my life shooting four or five spurts all the way up to his chin. At the same time, he thrust deep inside me and moaned one long moan as I felt his cock jerk several times deep in my ass. He slowly withdrew and I fell on the bed next to him completely drained. I felt wide open and remember thinking my ass would never recover.
Recover it did only to be assaulted again in the future. Me and the guy met several more times and jerked and sucked each other, but never fucked again.