When I was younger, I had a good friend, Rob, who I used to hang out with all the time. We’d talk about everything and were very close. At one point, I knew he’d gone through a long dry stretch sexually and was very frustrated with it. One night, we were hanging out together and he asked me if I could give him a blowjob. I was taken aback by it, but I’ve always been a pleaser, someone who wants the people in my life to be happy. After a back and forth, he talked me into doing it as a favor to one of my closest friends and, to my surprise, I enjoyed giving him head and swallowing his cum. I gave him several more blowjobs after that.
One night when I was going down on him, Rob asked me if he could fuck me. I looked up at him, shocked by the question. “Are you kidding me?” I asked.
“You haven’t thought about it before?” he replied. “I’m curious what it would be like.”
“No, I’ve never thought about it,” I said, although I had to admit there was a little bit of curiosity now creeping into my mind.
“Come on, man, we can just try it. No one will ever know,” Rob cajoled me. “Try it and I’ll stop if you don’t like it, I swear.” He kept after me quite a bit, as I kept saying no, but eventually I agreed to at least try it.
I stripped naked and climbed up on Rob’s bed, getting down on all fours with my ass up in the air. Rob got a tube of lubricant and I could feel it cold on my asshole as he squeezed some on me, then began lubricating his cock. “You ready?” he asked, kneeling down behind me and beginning to press his cock against my asshole.
“Not really,” I replied. He laughed and grabbed me by my hips with one hand, as he guided his cock into my asshole with the other. He was probably not even halfway into me when the pain became excruciating. Rob had a pretty large cock–like about 8″ and thick–so I was immediately thinking this was not the best idea. I immediately pushed back on him, telling him to stop. He resisted me, his cock still partway in my ass. “Just relax,” he said. “You’ll get used to it. It feels really good being in you.”
But the pain was way too much to bear. I insisted he pull out of me. We went back and forth for I don’t know how long, but finally he gave up and pulled out of me.
I was embarrassed about that night for some time, but neither of us mentioned it. Until one night some time later, we were hanging out drinking some beers and I have to admit, I was feeling really horny. I asked Rob if he’d like to try fucking me again. His face lit up immediately, “Are you serious?”
“Yes, let’s try it again,” I replied.
“Yeah, I want to try it again. I have an idea too,” he said. I stripped naked as Rob went and got a towel and laid it down on the floor. “Lay down on your back,” he told me, motioning toward the towel and he took off his clothes.
I did as he told me and watched as he began to apply lubricant to his cock, then reached between my legs to rub lube on my ass. He got between my legs and took my legs in his hands, lifting them on to his shoulders. I felt his cock push against my asshole. I closed my eyes, in anticipation of the pain of him going inside of me.
My eyes closed, I felt his cock slide into me, inch by inch. And to my surprise, while there was a small amount of discomfort at first, as he worked his cock into me, I relaxed more. I realized after a bit that his whole cock was inside me and he was beginning to fuck me. I opened my eyes and looked up at him. My legs were up over his shoulders and he was fucking my ass, his cock going in and out of me slowly.
And not only was he fucking me with no pain, I realized, it felt really good having his cock pushing in and out of my mouth. My mind was racing at how good this felt. I had never imagined I would enjoy having another man fuck my ass, but now I realized that not only was I enjoying it, my own cock was suddenly rock hard from the feeling.
“Oh god,” I heard my own voice moan, “Fuck me.” I couldn’t believe what I was saying, but I had no control over the words coming out of my mouth. Rob picked up the pace and began to fuck me a bit faster, holding on to my hips. “Fuck me harder,” I heard myself beg him and he began to drive his cock deeper and harder into my ass. He was definitely all the way deep in me now and picked up the pace further as I heard myself beg him again to give it to me harder and harder. At one point, he started to touch my throbbing dick and I had to push his hand away, because I was afraid I would cum all over myself if he touched me while he fucked me.
I was out of control at that point, demanding that he fuck me harder as he obliged and slammed his cock in and out of my ass. I don’t know how long this lasted, but before I know it, he was thrusting deep in me, telling me he was going to cum. I was panting, sweating, my eyes squeezed shut as I felt him shoot cum deep inside me, then slowly withdraw his softening cock from my ass. My own cock was still so hard and as Rob went to the bathroom to clean up, I began to touch my own cock, quickly cumming all over myself from all of the stimulation I’d received.
My mind was struggling at that point to process what I’d just experienced. I could not believe that I had just heard myself begging and begging to be fucked hard and deep, like some desperate little slut, that’d taken a big fat cock all the way in my ass and was now dripping cum. I couldn’t believe that I found myself wanting to do it again.
Source: reddit.com/r/gonewildstories/comments/8rispm/mm_first_time_fucked_and_creampied
This made me so hard hot story