Well then, let’s try and put in words my first fuck, anally with a guy I mean. It happened when I was at university and whilst having a ‘relationship’ with a guy called Mike. For a few weeks we had been playing around, wanking, licking, sucking, just general fun. We had even progressed to fingering each other’s ass sometimes, but not too often.
Then one morning as we were playing with each other’s cock, and I was fingering Mike’s asshole, he said, totally unexpectedly, that he wanted my cock in there instead of a finger. I had often wondered what it would be like to fuck a guy, so I asked him if he was sure and he replied that he was. He asked me if I was agreeable with that and I remarked that I was if he was. He stated that he had some Vaseline, so he got up and arrived back with a tube of it. Returning to bed, he assumed the doggie position. As a virgin at this I was a little nervous but I smeared some, well actually loads of, Vaseline all over my, by then, hard and pulsing cock and some on and in Mike’s asshole.
I knelt on the bed behind him, between his calves and moved in. Again I asked him if he was sure about doing it and he groaned a “Yes”.
So I held his arse cheeks and pulled them apart, seeing in full stare his arse eye. Then releasing one hand I took my hard cock and placed the purple head against his hole. I wiggled my arse a bit and tried to move my hips, and consequently my cock, forward. I wanted my cock helmet to enter the dark cavern within. However he was so tight, closed in fact, so that I couldn’t get in at all. His sphincter muscle had closed up solid. He was frightened and I was very apprehensive. So I tried again, telling him to relax and again nothing. However on the third attempt my cock tip just entered through the start of his anal gate. My cock end and cum slit moved in a little stretching his ring slightly.
Mike moaned a grunt, not out of joy, but out of pain. I was a little frightened but he said to carry on. So I moved in further and my cock head started going into his ass. Half my cock-head at first as I moved in slowly. I held his hips as, by now, my cock knew its way in. Another little shove and my cock-head was fully past his ass ring. But as it popped in, Mike said it was too painful so I pulled out all the way. My cock isn’t long but it is quite meaty. By then it was a solid rod, bouncing in front of me with every free move I made. I put some more Vaseline on it and moved back in once more. Again, I got into his ass entrance and soon I was cock-head deep in him humping his asshole but just with my glans deep. His tightness had forced my foreskin to roll back exposing my frenulum, that horny sweet spot which I love being rubbed. I moved in another inch but having my foreskin pulled back so far made it start to hurt me. As his ring grip on my cock was very tight we were both in pain, oh deep fun!!