[M]y first anal experience left me wanting [m]ore | 2016

Quick and dirty intro. I am 28, male, white, average build. Living in the city, going to school. I have been experimenting with men since I was 17 on and off. Nothing more than jerking off together, handjobs, blowjobs. No one knows about this but the few guys that are keeping my secrets. After a 5 year dry spell I started a on and off thing with another guy, about 10 years older than me for the last few months, we have met and given each other blow jobs four times now. Each time only one of us sucking the other. When we first met we showed each other our recent results to be sure we wouldn't catch anything. The two times he blew me I would be sitting on his couch studying for school while he sucked me, I would cum in his mouth and he would go spit it out in the sink. When I blew him he would lay down, I would suck him until he came in my mouth and I would swallow it and clean any remaining cum from him. The last time we met was a few days ago. He came over to my place (all times previous we have met at his condo), we both knew what was in order already so when he arrived I sat down and he proceeded to tug off my pants and took my dick into his mouth. He had to have been sucking me for a good ten minutes before his phone rang and he stopped. He explained that he needed to take this call. I didn't mind at all, he has had to take calls before. What happened next was a total surprise to me. He dropped his pants and boxers, got up on the couch and straddling my face he pushed his dick into my mouth. I was surprised but started sucking anyways. Almost immediately he pushed further in until i was starting to gag on his dick and I was trying so hard not to start gagging or making noise because he was on the phone. For some reason this was a huge turn on for me because I found I was instantly rock hard. When he got off the phone he put both hands on my head and slowly pushed his dick down my throat until my nose was pushing into his pubes. He pulled his dick out and I coughed a bit, he asked me if I was alright and I said yeah. He told me how amazing it had felt and told me to hold still for a minute while he proceeded to slap my face and lips with his cock. Amazingly enough I found myself turned on even more. What happened next is making me hard just writing about it. He told me to turn around, to not worry, to just relax. (I have never had anal sex before, I have been fingered, and rimmed but never been penetrated.) I felt an amazing mix of excitement and nervousness. Getting up and turning around I bent over, steadying myself on the edge of the couch, keeping my legs straight to expose my ass as much as possible. The next thing i felt was his semi-hard very warm dick pressed against my ass vertically between my cheeks. It was absolutely amazing. Spitting on his dick and my ass he provided enough lubrication to begin running his dick in an up and down motion between my cheeks, gradually spreading them more and more until the mushroom tip was brushing past my asshole. I am pretty sure I was so turned on that I might have cum from him doing that alone had he continued. I know he must have sensed that I was enjoying it because he then pushed his hips forward into me and began moving up and down with the entire length of his dick now vertical between my cheeks in a slow mock fucking motion. I felt like I was getting a sort of special massage and I didn't want it to stop. I felt him pull back a little and was afraid for a minute that we were done, that he wanted me to go back to sucking him. But then I felt the head of his dick pressing directly on my asshole. I couldn't think straight. I remember only being able to moan a bit and he took that as the go signal because the next thing I felt was pressure pushing on my ass. It was a bit of bumping mixed with wiggling and angle adjustment from his side. After what seemed like forever I felt him inside me. I thought I was going to die it felt so much bigger than it did in my mouth. I think he knew this because he told me to relax, it was just the tip of his dick. He pulled out and pushed back inside only once more before he pulled out and had me stand up. Getting back on his knees he began sucking my dick again and reaching up behind me he started massaging my asshole which made me cum almost instantly. I cant remember the last time I had such a powerful cum, I ended up bent over with a hand on his shoulder and the other on the back of his head and getting so lightheaded I thought I would pass out. After that I felt a bit awkward. He explained to me that we were done, he had a meeting to get to and had cum earlier that morning so there was really no use in trying to finish him off. I was fine with that. Once he left I flopped down on the couch and turned on the tv and just let my mind stay blank for a while. 

Later that day I started thinking about our encounter. Started thinking about his dick on my ass and got rock hard instantly. I hastily dispatched that erection, washed my hands and got to writing my buddy an email. I thanked him for coming by. And I explained to him that I had been thinking it over and I really wanted to meet again soon and really try having him fuck me. I got a response about 5 minutes later. He agreed, told me that today was really hot for him and he would be eager to meet again. "I would be down to go further next time- going into you and pumping my load into you..." I wrote back saying yes yes and yes. We will be meeting next week. I cannot wait.