27[MM] The time one of the straight guys I'd been sucking off asked if he could go further | 2016

I've written a couple of times about how I've given blowjobs to straight guy friends of mine when they've been having periods of sexual frustration. It was win-win for us. I enjoyed pleasuring them. They got some much needed release. We kept it our mutual secret and that added to the all around turn on. Then one of them asked if he could fuck me. We'll call him John.

I was a little shocked when John asked if he could fuck me, as I hadn't really considered it before. Sucking his cock was just sort of fooling around, as I was fluid in my sexuality, and besides, he had kind of a big dick at 7'5" and thick. So I was super nervous, but I agreed to try it.

The first couple of times, big no way. The first time we tried, we did it doggy style on his bed and it hurt way too much when he tried to put it in me. The second time, his roommate was out of town and he had me bend over their couch. When he tried to put it in me, I almost screamed. Sorry, I told him, not going to work.

The third time around, he talked me into trying it one last time, as he had a different idea. I happened to be super horny at the time, so I was willing to give it a shot. This time, John had me lay on my back on the floor of his bedroom. He picked my legs up over his shoulders as he spread them and began to slide his lubed up cock into my ass. Amazingly, it slid right in with just the smallest bit of pain.

As he pushed further into my ass slowly, I was amazed to realize how far into me he was penetrating. I closed my eyes and relaxed and before I knew it, he had his cock all the way up my ass. "I'm gonna start fucking you now, ok?" he asked. I nodded, my eyes still closed. He began to slide his cock out of my ass and then back in and somewhere inside me, I began to realize I was enjoying the feeling. As he kept going, I heard this voice come from somewhere outside of my body, "Fuck me harder!"

Oh, shit, did I say that? I don't know what had come over me, but there I was, as he pushed his cock in and out of my ass, my legs up in the air over his shoulders and as he did, I could hear myself now begging him, "Fuck me harder! Fuck me harder!" I was begging him now and couldn't control myself as he fucked me harder and harder as I was almost shouting now. I don't know how long this lasted, but when he came, we both nearly collapsed. I realized my own dick was rock hard from him fucking me as he pulled out of my ass and I found myself embarrassed at how out of control I'd gotten, but so turned on by how it had made me feel. Never in my wildest dreams would I ever have known that I'd get off that much by being fucked in the ass, to the point where I was nearly possessed, begging like a dirty little slut to have more of that cock pounding me deep.